Chiral separation techniques: a practical approach
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| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Weinheim
WILEY-VCH
2007
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| Edition: | 3., completely rev. and updated ed. |
| Subjects: | |
| Online Access: | Inhaltstext Klappentext Inhaltsverzeichnis |
| Physical Description: | XXII, 618 S. Ill., graph. Darst. |
| ISBN: | 9783527315093 |
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| 245 | 1 | 0 | |a Chiral separation techniques |b a practical approach |c ed. by Ganapathy Subramanian |
| 250 | |a 3., completely rev. and updated ed. | ||
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2007 | |
| 300 | |a XXII, 618 S. |b Ill., graph. Darst. | ||
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| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Chirality |x Industrial applications | |
| 650 | 4 | |a Enantiomers |x Separation | |
| 650 | 4 | |a Liquid chromatography | |
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Record in the Search Index
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| adam_text | Chirality describes the fact that a particular molecule can have a right-
hand structure or its mirrored left-hand structure, both of which
may display very different characteristics. For example, a right-hand
structure can be an important active substance for a drag while its
left-hand variation is highly toxic. For this reason, chiral separation
techniques are indispensable for production and safety testing in bio¬
technology, food and pharmaceutical industries.
Thoroughly revised, with either entirely new or completely updated
contents, this is a practical manual for the small and large-scale prepara¬
tion of enantiomerkally pure products. The result is a vital resource for
meeting the highest purity standards in the manufacture of chiral phar-
maceuticals, food additives and related compounds. All the approaches
covered here are highly relevant to modern manufacturing and quality
control schemes in the pharmaceutical and biotech industries, address¬
ing the increasingly important issue of drug safety in view of tougher
regulatory standards worldwide.
With over
30
years experience in both industry and
academia,
Canapathy Submmanmn
¡s a
biotechnolog/
consultant
working in the application and development of processing,
purification methodologies and chromatographic systems for
large-scale use in environmental science, food
sdente,
per¬
fumer/ cosmetics and Pharmaceuticals. He has also taught
extensively in the area of food and medical technology.
A chemistry graduate from Madras, India, he gamed his
doctorate from the University of Glasgow for work on natural
products, and his mam research interests he
m
the utilization
of natural
mattnál
separation processes and bio-conversions,
Dr,
Subramaman has written and edited a number of
books and articles
m
the field ofbiotechnohgy. For the fast
to years, he has been crganmng conferences promoting the
integration and knowledge etchange between
academia
and
industry.
CHIRAL SEPARATION TECHNIQUES A PRACTICAL APPROACH EDITED BY GANAPATHY
SUBRAMANIAN 3RD, COMPLETELY REVISED AND UPDATED EDITION AIONTIIHIAL
BICENTINHI WILEY-VCH VERLAG GMBH & CO. KGAA CONTENTS PREFACE XVU LIST OF
CONTRIBUTORS XJX 1 METHOD DEVELOPMENT AND OPTIMIZATION OF
ENANTIOSEPARATIONS USING MACROCYCLIC CLYCOPEPTIDE CHIRAL STATIONARY
PHASES 1 THOMAS E. BEESLEY CMDJ. T. LEE 1.1 INTRODUCTION 1 1.2
STRUCTURAL CHARACTERISTICS OF MACROCYCLIC GLYCOPEPTIDE CSPS 2 1.2.1
CHIRAL RECOGNITION MECHANISMS 2 1.2.2 MULTI-MODAL CHIRAL STATIONARY
PHASES 5 1.3 ENANTIOSELECTIVITY AS A FUNCTION OF MOLECULAR RECOGNITION 6
1.3.1 IONIZABLE MOLECULES 6 1.3.1.1 POLAR IONIC MODE 6 1.3.1.2
REVERSED-PHASE MODE 9 1.3.2 NEUTRAL MOLECULES 9 1.4 COMPLEMENTARY
EFFECTS 12 1.5 METHOD DEVELOPMENT 12 1.6 OPTIMIZATION PROCEDURES 15
1.6.1 POLAR IONIC MODE 15 1.6.2 REVERSED-PHASE MODE 19 1.6.2.1 PH
EFFECTS 19 1.6.2.2 ORGANIC MODIFIER EFFECTS 20 1.6.3 POLAR
ORGANIC/NORMAL-PHASE MODE 21 1.6.4 FLOW-RATE AND TEMPERATURE EFFECTS 22
1.7 AMINO ACID AND PEPTIDE ANALYSIS 23 1.8 CONCLUSION 27 ACKNOWLEDGMENTS
27 REFERENCES 27 CHIRAL SEPARATION TECHNIQUES. THIRD EDITION. EDITED BY
G. SUBRAMANIAN COPYRIGHT 207_WILEY-VCH VETLAG GMBH & CO KCAA,
WEINHEIM ISBN: 978-3-527 31509 3 VI ] CONTENTS 2 ROLE OF POLYSACCHARIDES
IN CHIRAL SEPARATIONS BY LIQUID CHROMATOGRAPHY AND CAPILLARY
ELECTROPHORESIS 29 IMRAN ALL AND HASSAN Y. ABOUL-ENEIN 2.1 INTRODUCTION
29 2.2 STRUCTURES OF POLYSACCHARIDE CHIRAL SELECTORS 30 2.2.1 SYNTHESIS
OF POLYSACCHARIDE CHIRAL SELECTORS 32 2.2.2 PREPARATION OF
POLYSACCHARIDE CHIRAL STATIONARY PHASES 33 2.2.2.1 PREPARATION OF CSPS
BY COATING 34 2.2.2.2 PREPARATION OF CSPS BY IMMOBILIZATION 34 2.2.2.3
COATED VERSUS IMMOBILIZED CSPS 41 2.3 PROPERTIES OF POLYSACCHARIDE CSPS
41 2.3.1 ENANTIOSELECTIVITIES 42 2.3.2 SPECTROSCOPIC STUDIES 45 2.4
APPLICATIONS 48 2.4.1 ANALYTICAL SEPARATIONS 48 2.4.2 PREPARATIVE
SEPARATIONS 50 2.5 OPTIMIZATION OF CHIRAL SEPARATIONS 53 2.5.1 MOBILE
PHASE COMPOSITIONS 54 2.5.2 PH OF THE MOBILE PHASE 64 2.5.3 FLOW-RATE 64
2.5.4 TEMPERATURE 68 2.5.5 STRUCTURES OF SOLUTES 72 2.5.6 OTHER
PARAMETERS 76 2.6 CHIRAL RECOGNITION MECHANISMS 76 2.7 CHIRAL SEPARATION
BY SUB- AND SUPERCRITICAL FLUID CHROMATOGRAPHY 80 2.8 CHIRAL SEPARATION
BY CAPILLARY ELECTROCHROMATOGRAPHY 84 2.9 CHIRAL SEPARATION BY
THIN-LAYER CHROMATOGRAPHY 87 2.10 CHIRAL SEPARATION BY CAPILLARY
ELECTROPHORESIS 88 2.11 CONCLUSION 90 REFERENCES 91 3 ANALYTICAL AND
PREPARATIVE POTENTIAL OF IMMOBILIZED POLYSACCHARIDE-DERIVED CHIRAL
STATIONARY PHASES 99 TONG ZHANG AND PILAR FRANCO 3.1 INTRODUCTION 99
3.1.1 SCIENTIFIC DEVELOPMENTS IN POLYSACCHARIDE IMMOBILIZATION WITH
CHIRAL RECOGNITION PURPOSES 100 3.1.2 STATE OF THE ART ON IMMOBILIZED
POLYSACCHARIDE-DERIVED CSPS 104 3.2 SCOPE OF IMMOBILIZED
POLYSACCHARIDE-DERIVED CSPS 105 3.3 BENEFICIAL CHARACTERISTICS OF
IMMOBILIZED POLYSACCHAIIDE-DERIVED CSPS 106 3.3.1 MEW SELECTIVITY
PROFILE ON IMMOBILIZED CSPS 107 CONTENTS VII 3.3.2 UNIVERSAL MISCIBILITY
OF NON-STANDARD SOLVENTS AND THEIR CONTRIBUTION TO THE PERFORMANCE OF
ANALYTICAL METHODS 110 3.3.3 VARIOUS SAMPLE INJECTION MEDIA 113 3.3.4
INHIBITION OR MINIMIZATION OF RACEMIZATION BY MOBILE PHASE SWITCH 116
3.3.5 PREPARATIVE POTENTIAL OF IMMOBILIZED CSPS 118 3.3.6 CSP STABILITY
120 3.4 METHOD DEVELOPMENT ON IMMOBILIZED POLYSACCHARIDE-DERIVED CSPS
122 3.4.1 SELECTION OF THE MOBILE PHASE 122 3.4.1.1 ANALYTICAL METHOD
DEVELOPMENT 122 3.4.1.2 PREPARATIVE METHOD DEVELOPMENT 125 3.4.2 MOBILE
PHASE ADDITIVES 126 3.4.3 A POWERFUL HYPHENATION: DAD-ELSD 126 3.5
REGENERATION OF IMMOBILIZED CSPS - WHY, HOW AND WHEN 129 3.6 CONCLUSIONS
AND PERSPECTIVES 132 REFERENCES 132 4 CHIRAL SEPARATIONS USING
SUPERCRITICAL FLUID CHROMATOGRAPHY 135 KAREN W. PHINNEY AND RODGER W.
STRINGHAM 4.1 INTRODUCTION 135 4.2 OVERVIEW OF SFC 135 4.2.1 PROPERTIES
OF SUPERCRITICAL FLUIDS 135 4.2.2 COMPARISON OF LC AND SFC 137 4.2.3
INSTRUMENTATION FOR SFC 138 4.3 CHIRAL STATIONARY PHASES IN SFC 139
4.3.1 CYDODEXTRINS 140 4.3.2 BRUSH-TYPE (PIRKLE-TYPE) 140 4.3.3
MACROCYCLIC ANTIBIOTICS 141 4.3.4 POLYSACCHARIDES 141 4.4 MOBILE PHASE
EFFECTS IN SFC 142 4.4.1 PRESSURE EFFECTS 142 4.4.2 FLOW-RATE EFFECTS
143 4.4.3 TEMPERATURE EFFECTS 143 4.4.4 MOBILE PHASE MODIFIER EFFECTS
144 4.4.5 MOBILE PHASE ADDITIVE EFFECTS 147 4.5 PREPARATIVE-SCALE
SEPARATIONS 148 REFERENCES 152 5 CHIRAL SEPARATION BY LIGAND EXCHANGE
155 GERALD CUBITZ AND MARTIN C. SCHMID 5.1 I NTRODUCTION 155 5.2 CHIRAL
LIGAND-EXCHANGE CHROMATOGRAPHY 156 VIII CONTENTS 5.2.1 SEPARATION BY LC
ON CHEMICALLY BONDED CHIRAL STATIONARY LE PHASES 156 5.2.2 SEPARATION BY
HPLC ON CHIRAL COATED LE PHASES 161 5.2.3 SEPARATION BY HPLC USING
CHIRAL ADDITIVES TO THE MOBILE PHASE 164 5.2.4 SEPARATION BY LE-TLC 164
5.3 COMPLEXATION GAS CHROMATOGRAPHY 165 5.4 LE-ELECTROMIGRATION
TECHNIQUES 165 5.4.1 SEPARATION BY CAPILLARY ZONE ELECTROPHORESIS (CZE)
165 5.4.2 SEPARATION BY MICELLAR ELECTROKINETIC CHROMATOGRAPHY (MEKC)
171 5.4.3 SEPARATION BY MICRO-CHANNEL CHIP ELECTROPHORESIS 172 5.4.4
SEPARATION BY CAPILLARY ELECTROCHROMATOGRAPHY (CEC) 172 LIST OF
ABBREVIATIONS 175 REFERENCES 176 6 ADVANCES IN SIMULATED MOVING BED
CHROMATOGRAPHIC SEPARATIONS 181 PEDRO S6 GOMES, MIRJANA MINCEVA, LUIS S.
PAIS, AND ALIRIO E. RODRIGUES 6.1 INTRODUCTION 181 6.2 MODELING
STRATEGIES 183 6.2.1 REAL SMB 183 6.2.1.1 DETAILED PARTICLE MODEL 184
6.1.2.1 LINEAR DRIVING FORCE APPROACH 186 6.2.2 EQUIVALENT TMB 186
6.2.2.1 DETAILED PARTICLE MODEL 187 6.2.2.2 LDF APPROACH 289 6.3
SIMULATION 189 6.3.1 NUMERICAL SOLUTION 189 6.3.2 CASE STUDY: OPERATING
CONDITIONS AND MODEL PARAMETERS 190 6.3.3 SIMULATIONS RESULTS 191
6.3.3.1 REAL SMB MODELS 191 6.3.3.2 EQUIVALENT TMB MODELS 194 6.4 NOVEL
SMB CONFIGURATIONS 195 6.4.1 VARICOL AND MULTIPLE FEED SMB 195 6.4.1.1
VARICOL 195 6.4.1.2 MULTIPLE (DISTRIBUTED) FEED 198 6.5 IMPROVEMENTS IN
OPERATION CONDITIONS EVALUATION (SEPARATION VOLUME METHOD} 200 6.6
CONCLUSIONS 201 REFERENCES 201 CONTENTS I IX 7 LESS COMMON APPLICATIONS
OF ENANTIOSELECTIVE HPLC USING THE SMB TECHNOLOGY IN THE PHARMACEUTICAL
INDUSTRY 203 STEFONIE ABEL AND MARKUSJUZA 7.1 INTRODUCTION - FROM AN
EMERGING TECHNOLOGY TO A CLASSICAL UNIT OPERATION 203 7.1.1 LESS COMMON
APPLICATIONS OF SMB TECHNOLOGY FOR CHIRAL SEPARATIONS 206 7.1.2 DESIGN
AND OPTIMIZATION OF OPERATING CONDITIONS FOR A CLASSICAL SMB SEPARATION
208 7.1.3 CHIRAL STATIONARY PHASES 211 7.2 UNBALANCED SEPARATIONS AND
MULTI-COMPONENT SEPARATIONS USING SMB 213 7.2.1 BINARY SEPARATIONS 214
7.2.1.1 CASE STUDY I: 1:1 VS. 10:1 AND 1:10 215 7.2.2 THREE-COMPONENT
SEPARATIONS 217 7.2.2.1 CASE STUDY II: THREE-COMPONENT SEPARATIONS WITH
TWO TARGETS 218 7.2.3 MULTI-COMPONENT SEPARATIONS VIA SMB 221 7.2.3.1
CASE STUDY III: MULTI-COMPONENT SEPARATION 221 7.2.4 GENERALIZED RULES
FOR OPTIMIZING UNBALANCED AND MULITCOMPONENT SEPARATIONS VIA SMB 223
7.2.4.1 DETECTING PROBLEMS 223 7.2.4.2 SOLVING PROBLEMS 225 7.3 UNUSUAL
ISOTHERMS AND ADSORPTION BEHAVIOR 225 7.3.1 LANGMUIR ADSORPTION ISOTHERM
226 7.3.2 NON-LANGMUIR ADSORPTION ISOTHERMS 227 7.3.2.1 PEAK SHAPE AND
FORM OF LINEAR AND ANTI-LANGMUIR ISOTHERMS 229 7.3-2.2 REGION OF
COMPLETE SEPARATION FOR AN ANTI-LANGMUIR ISOTHERM 230 7.3.3 CASE STUDIES
231 7.3.3.1 CASE STUDY IV: BOTH COMPOUNDS SHOW ANTI-LANGMUIRIAN BEHAVIOR
232 7.3.3.2 CASE STUDY V: ONE COMPOUND SHOWS ANTI-LANGMUIRIAN BEHAVIOR
234 7.3.4 GENERAL TRENDS FOR LOADING STUDIES AND ADSORPTION ISOTHERMS
237 7.4 APPLICATIONS OF VARIOUS COLUMN CONFIGURATIONS 237 7.4,1
SYMMETRICAL CONFIGURATIONS 237 7.4.1.1 CASE STUDY VI: COMPARING A
2-2-2-2 AND A 1-2-2-1 CONFIGURATION 240 7.4.1 ASYMMETRIC CONFIGURATIONS
241 7.5 APPLICATION OF SOLVENT GRADIENTS 243 7.5.1 SOLVENT GRADIENT SMB
244 7.5.1.1 CASE STUDY VII: PREPARATIVE-SCALE SMB APPLYING A REVERSED
SOLVENT GRADIENT 247 7.6 CHEMISTRY AND RACEMIZATION 251 7.6.1
RACEMIZATION 253 7.6.2 CASE STUDIES 257 X I CONTENTS 7.6.2.1 CASE STUDY
VIII: ASBAT INHIBITOR 257 7.6.2.2 CASE STUDY IX . ANTIDEPRESSANT OXETINE
DERIVATIVES 258 7.6.2.3 CASE STUDY X: ZOLOFT, A SEROTONIN REUPTAKE
INHIBITOR 259 7.6.2.4 CASE STUDY XI: SYNTHESIS OF ENANTIOMERICALLY PURE
AMINES VIA SCHIFF BASES 262 7.6.2.5 CASE STUDY XII: SYNTHESIS OF COX-2
INHIBITORS 263 7.7 FUTURE DEVELOPMENTS 264 7-7.1 NON-HPLC
ENANTIOSELECTIVE SMB MODES 265 7.7.2 OPERATION MODES, MODELING SOFTWARE,
CONTROL OF SMB UNITS, AND STATIONARY PHASES 266 7.8 CONCLUSION 267
NOTATION 268 GREEK LETTERS 268 SUBSCRIPTS 268 ACKNOWLEDGMENTS 268
REFERENCES 269 3 ENANTIOMER SEPARATION BY CHIRAL CROWN ETHER STATIONARY
PHASES 275 MYUNG HO HYUN 8.1 INTRODUCTION 275 8.2 DEVELOPMENT OF CSPS
276 8.2.1 CSPS BASED ON CHIRAL CROWN ETHERS INCORPORATING A CHIRAL
L,L -BINAPHTHYL UNIT 276 8.2.2 CSPS BASED ON CHIRAL CROWN ETHERS
INCORPORATING A TARTARIC ACID UNIT 277 8.2.3 CSPS BASED ON PHENOLIC
PSEUDO CHIRAL CROWN ETHERS 281 8.3 APPLICATIONS OF CSPS 282 8.3.1
RESOLUTION OF PRIMARY AMINO COMPOUNDS 282 8.3.2 RESOLUTION OF
NON-PRIMARY AMINO COMPOUNDS 285 8.4 COMPOSITION OF MOBILE PHASE 288
8.4.1 AQUEOUS MOBILE PHASE 288 8.4.1.1 ORGANIC MODIFIER IN AQUEOUS
MOBILE PHASE 288 8.4.1.2 ACIDIC MODIFIER IN AQUEOUS MOBILE PHASE 290
8.4.1.3 INORGANIC CATIONIC MODIFIER IN AQUEOUS MOBILE PHASE 293 8.4.2
NONAQUEOUS MOBILE PHASE 294 8.5 TEMPERATURE EFFECT 295 8.6 CONCLUSION
297 ACKNOWLEDGMENT 298 REFERENCES 298 CONTENTS XI 9 ENANTIOSELECTIVE
SEPARATION OF AMINO ACIDS AND HYDROXY ACIDS BY LIGAND EXCHANGE WITH
COPPER(LL) COMPLEXES IN HPLC (CHIRAL ELUENT) AND IN FAST SENSING SYSTEMS
301 ROSANGETA MARCHELTI, ROBERTO CARRADINI, GIANNI GOIAVERNA, ARNALDO
DOSSENA, FRANCESCO DALLAVALLE, AND STEFANO SFORZA 9.1 INTRODUCTION 301
9.2 ENANTIOMERIC SEPARATION OF AMINO ACIDS AND HYDROXY ACIDS WITH THE
CHIRAL SELECTORS ADDED TO THE MOBILE PHASE IN HPLC (CMPS) 303 9.2.1
BIDENTATE LIGANDS 303 9.2.1.1 ENANTIOMERIC SEPARATION OF FREE D,L-AMINO
ACIDS 303 9.2.1.2 ENANTIOMERIC SEPARATION OF D,L-DNS-AMINO ADDS 308
9.2.1.3 ENANTIOMERIC SEPARATION OF A-HYDROXY ACIDS AND DICARBOXYLIC
ACIDS 309 9.2.2 TERDENTATE LIGANDS 312 9.2.2.1 ENANTIOSEPARATION OF
UNMODIFIED AMINO ACIDS 312 9.2.2.2 ENANTIOSEPARATIO N OF DNS-AMINO ACIDS
314 9.2.3 TETRADENTATE LIGANDS 315 9.2.3.1 ENANTIOMERIC SEPARATION OF
UNMODIFIED AMINO ACIDS 316 9.2.3.2 CHIRAL SEPARATION OF DNS-AMINO ACIDS
318 9.3 DYNAMICALLY COATED STATIONARY PHASES 319 9.4 COMPARISON BETWEEN
ENANTIOMERIC SEPARATIONS OBTAINED WITH THE CHIRAL SELECTOR BOUND TO THE
STATIONARY PHASE OR ADDED TO THE ELUENT 320 9.5 MIXED
INCLUSION-LIGAND-EXCHANGE CHROMATOGRAPHY 325 9.6 LIGAND EXCHANGE IN FAST
SENSING SYSTEMS 327 ACKNOWLEDGMENT 329 REFERENCES 329 10 ENANTIOMER
SEPARATION BY CAPILLARY ELECTROPHORESIS 333 GERHARD K. E. SCRIBA 10.1
INTRODUCTION 333 10.2 MODES OF CAPILLARY ELECTROMIGRATION TECHNIQUES 334
10.3 THEORY OF ELECTROPHORETIC SEPARATIONS 334 10.3.1 BASICS OF
CAPILLARY ELECTROPHORESIS 334 10.3.2 CHIRAL SEPARATIONS 335 10.4
ENANTIOMER SEPARATIONS 337 10.4.1 INDIRECT CHIRAL SEPARATIONS 338 10.4.2
DIRECT CHIRAL SEPARATIONS 338 10.4.2.1 CYCLODEXTRINS 343 10.4.2.2
MACROCYDIC ANTIBIOTICS 346 10.4.2.3 CHIRAL CROWN ETHERS 349 10.4.2.4
CHIRAL UGAND EXCHANGE 350 10.4.2.5 CHIRAL ION-PAIR REAGENTS 350 10.4.2.6
CHIRAL SURFACTANTS 351 XII CONTENTS 10.4.2.7 MISCELLANEOUS CHIRAL
SELECTORS 353 10.5 APPLICATIONS 354 10.6 METHOD DEVELOPMENT AND
VALIDATION 358 10.7 MIGRATION MODELS 362 10.8 ENANTIOMER MIGRATION ORDER
364 10.9 FUTURE TRENDS 365 REFERENCES 366 11 COUNTER-CURRENT
CHROMATOGRAPHY IN THE SEPARATION OF ENANTIOMERS 369 EVA P6REZ AND
CRISTINA MINGUILLON 11.1 INTRODUCTION 369 11.2 INSTRUMENTATION 3 71 11.3
SOME THOUGHTS ON CCC ENANTIOSEPARATION 372 11.4 CHIRAL SELECTORS USED IN
CCC ENANTIOSEPARATIONS 375 11.4.1 CHIRAL RECOGNITION IN THE AQUEOUS
PHASE 375 11.4.2 CHIRAL RECOGNITION IN THE ORGANIC PHASE 380 11.5
PH-ZONE-REFINING CCC 387 11.6 SAMPLE RESOLUTION IN CCC 392 11.7
CONTINUOUS CPC 393 11.8 CONCLUSIONS AND FUTURE TRENDS 394
ACKNOWLEDGMENTS 394 REFERENCES 395 12 SEPARATION OF ENANTIOMERS USING
MOLECULARLY IMPRINTED POLYMERS 399 BORJE SELLERGREN 12.1 INTRODUCTION
399 12.2 FUNDAMENTAL STUDIES USING ENANTIOMERS AS MODEL TEMPLATES 401
12.3 USING FRONTAL ANALYSIS TO ELUCIDATE RETENTION MECHANISMS 406 12.4
APPROACHES TO BINDING SITE DESIGN 412 12.4.1 COMBINATORIAL AND
COMPUTATIONAL TECHNIQUES TO OPTIMIZING MICSPS 413 12.4.2 MICSPS BY
RATIONAL DESIGN 415 12.5 OTHER FORMATS: BEADS, MONOLITHS, AND FILMS 418
12.5.1 BEADS AND NANOPARTIDES 419 12.5.2 LAYERS AND FILMS 421 12.5.3
SUPERPOROUS MONOLITHS 425 12.5.4 HIERARCHICAL IMPRINTING TECHNIQUES 426
12.6 OTHER MATRICES FOR IMPRINTING OF ENANTIOMERS 426 12.7 CONCLUSIONS
429 REFERENCES 429 CONTENTS XIII 13 ENANTIOSELECTIVE BIOSENSORS
RAIUCA-LOANA STEFAN-VAN STADEN, JACOBUS FREDERICK VAN STADEN, AND HASSAN
Y, ABOUL-ENEIN 433 13.1 I NTRODUCTION 433 13.2 THE DESIGN OF
ENANTIOSELECTIVE ELECTROCHEMICAL BIOSENSORS 433 13.3 APPLICATIONS OF
ENANTIOSELECTIVE ANALYSIS 434 13.3.1 AMINO ACIDS 434 13.3.2
ANGIOTENSIN-CONVERTING ENZYME INHIBITORS 434 13.3.3 THYROID HORMONES 435
13.3.4 ALANINE 435 13.3.5 CARNITINE AND O-ACETYL-L-CARNITINE 436 13.3.6
LYSINE 436 13.3.7 METHOTREXATE 437 13.3.8 PIPECOLIC ACID 437 13.4
CONCLUSION 438 REFERENCES 438 14 CHIRAL ANALYSIS IN CAPILLARY
ELECTROCHROMATOGRAPHY (CEC) AND CEC COUPLED TO MASS SPECTROMETRY 441 JIE
ZHENG AND SHAHAB A, SHAMS I 14.1 INTRODUCTION 441 14.2 CEC COLUMN
TECHNOLOGIES FOR CHIRAL SEPARATION 443 14.2.1 PACKED CAPILLARIES 443
14.2.2 OPEN-TUBULAR CAPILLARIES 445 14.2.3 MONOLITHIC CAPILLARIES 447
14.2.3.1 INORGANIC MONOLITH-BASED COLUMNS 447 14.2.3.2 ORGANIC POLYMERIC
MONOLITHIC COLUMNS 448 14.2.3.3 PARTICLE-LOADED MONOLITHIC COLUMNS 450
14.3 CHIRAL STATIONARY PHASES FOR CEC 45J 14.3.1 BRUSH-TYPE CSPS 453
14.3.2 CYCLODEXTRINS AND THEIR DERIVATIVES 456 14.3.3 MACROCYCLIC
GLYCOPEPTIDE-BONDED CSPS 460 14.3.4 POLYSACCHARIDE-BASED CSPS 466 14.3.5
PROTEIN-BASED CSPS 473 14.3.6 MOLECULAR IMPRINTING-BASED CSPS 475 14.3.7
LIGAND EXCHANGE-BASED CSPS 477 14.3.8 ION EXCHANGE-BASED CSPS 479 14.3.9
MISCELLANEOUS 483 14.4 CHIRAL CEC COUPLED TO MASS SPECTROMETRIC
DETECTION 485 14.4.1 CEC/MS INSTRUMENTATION AND COLUMN TECHNOLOGY 486
14.4.2 CHIRAL CEC/MS APPLICATIONS 491 14.5 CONCLUSIONS 499 LIST OF
ABBREVIATIONS 500 REFERENCES 50I XIV I CONTENTS 15 CHIRAL ANALYSIS USING
POLYMERIC SURFACTANTS IN MICELLAR ELECTROKINETIC CHROMATOGRAPHY (MEKC)
AND MEKC COUPLED TO MASS SPECTROMETRY 505 SYED A. A. RIZVI AND SHAHAB A.
SHAMSI 15.1 INTRODUCTION 505 15.2 CHIRAL ANIONIC SURFACTANTS 509 15.2.1
AMINO ACID-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS WITH AMIDE LINKAGE
509 15.2.2 PEPTIDE-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS WITH AMIDE
LINKAGE 525 15.2.3 AMINO ACID-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS
WITH CARBAMATE LINKAGE 537 15.3 CHIRAL CATIONIC SURFACTANTS 544 15.3.1
SINGLE AMINO ACID-BASED CATIONIC SURFACTANTS WITH AMIDE LINKAGE 544 15.4
COUPLING OF MEKC TO MASS SPECTROMETRY USING POLYMERIC SURFACTANTS 545
15.4.1 MEKC/MS METHOD DEVELOPMENT 547 15.4.2 MEKC/MS OF
()-L,L -BINAPHTHOL (BOH) 548 15.4.3 MEKC/MS OF ^-BLOCKERS 550 15.4.4
MEKC/MS OF BENZODIAZEPINES AND BENZOXAZOCINE 555 15.5 CONCLUSIONS 556
ACKNOWLEDGMENT 557 LIST OF ABBREVIATIONS 557 REFERENCES 559 16
POLARIMETER CHIRAL DETECTORS IN ENANTIOSEPARATIONS 561 GARY W. YANIK
16.1 INTRODUCTION 561 16.2 THEORY OF OPERATION 562 16.3 COMPARISON WITH
UV AND CD DETECTION 565 16.4 USEFUL DEFINITIONS 565 16.4.1 CHEMICAL
PURITY (CP) 565 16.4.2 ENANTIOMERIC PURITY (EP) 566 16.4.3 ENANTIOMERIC
EXCESS {EE) 566 16.4.4 SPECIFIC ROTATION SR) 566 16.5 AUTOMATION OF
METHOD DEVELOPMENT AND PREPARATIVE PURIFICATIONS 566 16.6 METHOD
DEVELOPMENT 568 16.7 PREPARATIVE PURIFICATIONS 569 16.8 ANALYTES 572
16.8.1 SMALL MOLECULE PHARMACEUTICAL CANDIDATES 572 16.8.2 ANTIBIOTICS
AND SUGARS: COMPOUNDS WITHOUT CHROMOPHORES 574 16.8.3 AMINO ACIDS 575
16.8.4 NATURAL PRODUCTS 575 CONTENTS XV 16.8.5 FOODS, FLAVORS, AND
FRAGRANCES 575 16.8.6 FERTILIZERS AND PESTICIDES 576 16.9 APPLICATIONS
577 16.9.1 ANALYSIS AND QA/QC 577 16.9.2 EXAMPLE: QA/QC OF ANTIBIOTIC
RESIDUES IN MILK - GENTAMICIN 577 16.9.3 HPLC/SFC METHOD DEVELOPMENT 580
16.9.4 HPLC/SFC PREPARATIVE PURIFICATION - FRACTION COLLECTION 580
16.9.5 PROCESS MONITORING 581 16.10 SUMMARY AND CONCLUSION 584
REFERENCES 584 17 PREPARATIVE CHIRAL CHROMATOGRAPHY - A POWERFUL AND
EFFICIENT TOOL IN DRUG DISCOVERY 585 SHAIINI ANCFERSSON 17.1
INTRODUCTION 585 17.2 CHIRAL CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERS
586 17.2.1 SELECTING THE CHIRAL STATIONARY PHASE 586 17.3 CHIRAL
PREPARATIVE CHROMATOGRAPHY PROCESS 588 17.3.1 COLUMN SCREEN AND
OPTIMIZATION 588 17.3.2 PREPARATIVE CHROMATOGRAPHY 590 17.3.2.1 CHOICE
OF THE CHROMATOGRAPHY MODE 590 17.3.2.2 LOADABILITY 593 17.3.2.3
SOLUBILITY 592 17 .4 EXAMPLES OF PREPARATIVE SEPARATION OF ENANTIOMERS
593 17.4.1 RESOLUTION OF DNZ-/?-PHENYLALANINE ISOMERS 593 17.4.2
RESOLUTION OF A CHIRAL ACID IN LATE-STAGE DISCOVERY PHASE 595 17.5
ANALYSIS AND CHIROPTICAL CHARACTERIZATION OF THE ISOLATED ENANTIOMERS
598 17.6 CONDUSIONS 598 REFERENCES 599 SUBJECT INDEX 601
|
| adam_txt |
Chirality describes the fact that a particular molecule can have a "right-
hand" structure or its mirrored "left-hand" structure, both of which
may display very different characteristics. For example, a "right-hand"
structure can be an important active substance for a drag while its
"left-hand" variation is highly toxic. For this reason, chiral separation
techniques are indispensable for production and safety testing in bio¬
technology, food and pharmaceutical industries.
Thoroughly revised, with either entirely new or completely updated
contents, this is a practical manual for the small and large-scale prepara¬
tion of enantiomerkally pure products. The result is a vital resource for
meeting the highest purity standards in the manufacture of chiral phar-
maceuticals, food additives and related compounds. All the approaches
covered here are highly relevant to modern manufacturing and quality
control schemes in the pharmaceutical and biotech industries, address¬
ing the increasingly important issue of drug safety in view of tougher
regulatory standards worldwide.
With over
30
years experience in both industry and
academia,
Canapathy Submmanmn
¡s a
biotechnolog/
consultant
working in the application and development of processing,
purification methodologies and chromatographic systems for
large-scale use in environmental science, food
sdente,
per¬
fumer/ cosmetics and Pharmaceuticals. He has also taught
extensively in the area of food and medical technology.
A chemistry graduate from Madras, India, he gamed his
doctorate from the University of Glasgow for work on natural
products, and his mam research interests he
m
the utilization
of natural
mattnál
separation processes and bio-conversions,
Dr,
Subramaman has written and edited a number of
books and articles
m
the field ofbiotechnohgy. For the fast
to years, he has been crganmng conferences promoting the
integration and knowledge etchange between
academia
and
industry.
CHIRAL SEPARATION TECHNIQUES A PRACTICAL APPROACH EDITED BY GANAPATHY
SUBRAMANIAN 3RD, COMPLETELY REVISED AND UPDATED EDITION AIONTIIHIAL
BICENTINHI WILEY-VCH VERLAG GMBH & CO. KGAA CONTENTS PREFACE XVU LIST OF
CONTRIBUTORS XJX 1 METHOD DEVELOPMENT AND OPTIMIZATION OF
ENANTIOSEPARATIONS USING MACROCYCLIC CLYCOPEPTIDE CHIRAL STATIONARY
PHASES 1 THOMAS E. BEESLEY CMDJ. T. LEE 1.1 INTRODUCTION 1 1.2
STRUCTURAL CHARACTERISTICS OF MACROCYCLIC GLYCOPEPTIDE CSPS 2 1.2.1
CHIRAL RECOGNITION MECHANISMS 2 1.2.2 MULTI-MODAL CHIRAL STATIONARY
PHASES 5 1.3 ENANTIOSELECTIVITY AS A FUNCTION OF MOLECULAR RECOGNITION 6
1.3.1 IONIZABLE MOLECULES 6 1.3.1.1 POLAR IONIC MODE 6 1.3.1.2
REVERSED-PHASE MODE 9 1.3.2 NEUTRAL MOLECULES 9 1.4 COMPLEMENTARY
EFFECTS 12 1.5 METHOD DEVELOPMENT 12 1.6 OPTIMIZATION PROCEDURES 15
1.6.1 POLAR IONIC MODE 15 1.6.2 REVERSED-PHASE MODE 19 1.6.2.1 PH
EFFECTS 19 1.6.2.2 ORGANIC MODIFIER EFFECTS 20 1.6.3 POLAR
ORGANIC/NORMAL-PHASE MODE 21 1.6.4 FLOW-RATE AND TEMPERATURE EFFECTS 22
1.7 AMINO ACID AND PEPTIDE ANALYSIS 23 1.8 CONCLUSION 27 ACKNOWLEDGMENTS
27 REFERENCES 27 CHIRAL SEPARATION TECHNIQUES. THIRD EDITION. EDITED BY
G. SUBRAMANIAN COPYRIGHT 207_WILEY-VCH VETLAG GMBH & CO KCAA,
WEINHEIM ISBN: 978-3-527 31509 3 VI ] CONTENTS 2 ROLE OF POLYSACCHARIDES
IN CHIRAL SEPARATIONS BY LIQUID CHROMATOGRAPHY AND CAPILLARY
ELECTROPHORESIS 29 IMRAN ALL AND HASSAN Y. ABOUL-ENEIN 2.1 INTRODUCTION
29 2.2 STRUCTURES OF POLYSACCHARIDE CHIRAL SELECTORS 30 2.2.1 SYNTHESIS
OF POLYSACCHARIDE CHIRAL SELECTORS 32 2.2.2 PREPARATION OF
POLYSACCHARIDE CHIRAL STATIONARY PHASES 33 2.2.2.1 PREPARATION OF CSPS
BY COATING 34 2.2.2.2 PREPARATION OF CSPS BY IMMOBILIZATION 34 2.2.2.3
COATED VERSUS IMMOBILIZED CSPS 41 2.3 PROPERTIES OF POLYSACCHARIDE CSPS
41 2.3.1 ENANTIOSELECTIVITIES 42 2.3.2 SPECTROSCOPIC STUDIES 45 2.4
APPLICATIONS 48 2.4.1 ANALYTICAL SEPARATIONS 48 2.4.2 PREPARATIVE
SEPARATIONS 50 2.5 OPTIMIZATION OF CHIRAL SEPARATIONS 53 2.5.1 MOBILE
PHASE COMPOSITIONS 54 2.5.2 PH OF THE MOBILE PHASE 64 2.5.3 FLOW-RATE 64
2.5.4 TEMPERATURE 68 2.5.5 STRUCTURES OF SOLUTES 72 2.5.6 OTHER
PARAMETERS 76 2.6 CHIRAL RECOGNITION MECHANISMS 76 2.7 CHIRAL SEPARATION
BY SUB- AND SUPERCRITICAL FLUID CHROMATOGRAPHY 80 2.8 CHIRAL SEPARATION
BY CAPILLARY ELECTROCHROMATOGRAPHY 84 2.9 CHIRAL SEPARATION BY
THIN-LAYER CHROMATOGRAPHY 87 2.10 CHIRAL SEPARATION BY CAPILLARY
ELECTROPHORESIS 88 2.11 CONCLUSION 90 REFERENCES 91 3 ANALYTICAL AND
PREPARATIVE POTENTIAL OF IMMOBILIZED POLYSACCHARIDE-DERIVED CHIRAL
STATIONARY PHASES 99 TONG ZHANG AND PILAR FRANCO 3.1 INTRODUCTION 99
3.1.1 SCIENTIFIC DEVELOPMENTS IN POLYSACCHARIDE IMMOBILIZATION WITH
CHIRAL RECOGNITION PURPOSES 100 3.1.2 STATE OF THE ART ON IMMOBILIZED
POLYSACCHARIDE-DERIVED CSPS 104 3.2 SCOPE OF IMMOBILIZED
POLYSACCHARIDE-DERIVED CSPS 105 3.3 BENEFICIAL CHARACTERISTICS OF
IMMOBILIZED POLYSACCHAIIDE-DERIVED CSPS 106 3.3.1 MEW SELECTIVITY
PROFILE ON IMMOBILIZED CSPS 107 CONTENTS VII 3.3.2 UNIVERSAL MISCIBILITY
OF NON-STANDARD SOLVENTS AND THEIR CONTRIBUTION TO THE PERFORMANCE OF
ANALYTICAL METHODS 110 3.3.3 VARIOUS SAMPLE INJECTION MEDIA 113 3.3.4
INHIBITION OR MINIMIZATION OF RACEMIZATION BY MOBILE PHASE SWITCH 116
3.3.5 PREPARATIVE POTENTIAL OF IMMOBILIZED CSPS 118 3.3.6 CSP STABILITY
120 3.4 METHOD DEVELOPMENT ON IMMOBILIZED POLYSACCHARIDE-DERIVED CSPS
122 3.4.1 SELECTION OF THE MOBILE PHASE 122 3.4.1.1 ANALYTICAL METHOD
DEVELOPMENT 122 3.4.1.2 PREPARATIVE METHOD DEVELOPMENT 125 3.4.2 MOBILE
PHASE ADDITIVES 126 3.4.3 A POWERFUL HYPHENATION: DAD-ELSD 126 3.5
REGENERATION OF IMMOBILIZED CSPS - WHY, HOW AND WHEN 129 3.6 CONCLUSIONS
AND PERSPECTIVES 132 REFERENCES 132 4 CHIRAL SEPARATIONS USING
SUPERCRITICAL FLUID CHROMATOGRAPHY 135 KAREN W. PHINNEY AND RODGER W.
STRINGHAM 4.1 INTRODUCTION 135 4.2 OVERVIEW OF SFC 135 4.2.1 PROPERTIES
OF SUPERCRITICAL FLUIDS 135 4.2.2 COMPARISON OF LC AND SFC 137 4.2.3
INSTRUMENTATION FOR SFC 138 4.3 CHIRAL STATIONARY PHASES IN SFC 139
4.3.1 CYDODEXTRINS 140 4.3.2 BRUSH-TYPE (PIRKLE-TYPE) 140 4.3.3
MACROCYCLIC ANTIBIOTICS 141 4.3.4 POLYSACCHARIDES 141 4.4 MOBILE PHASE
EFFECTS IN SFC 142 4.4.1 PRESSURE EFFECTS 142 4.4.2 FLOW-RATE EFFECTS
143 4.4.3 TEMPERATURE EFFECTS 143 4.4.4 MOBILE PHASE MODIFIER EFFECTS
144 4.4.5 MOBILE PHASE ADDITIVE EFFECTS 147 4.5 PREPARATIVE-SCALE
SEPARATIONS 148 REFERENCES 152 5 CHIRAL SEPARATION BY LIGAND EXCHANGE
155 GERALD CUBITZ AND MARTIN C. SCHMID 5.1 I NTRODUCTION 155 5.2 CHIRAL
LIGAND-EXCHANGE CHROMATOGRAPHY 156 VIII CONTENTS 5.2.1 SEPARATION BY LC
ON CHEMICALLY BONDED CHIRAL STATIONARY LE PHASES 156 5.2.2 SEPARATION BY
HPLC ON CHIRAL COATED LE PHASES 161 5.2.3 SEPARATION BY HPLC USING
CHIRAL ADDITIVES TO THE MOBILE PHASE 164 5.2.4 SEPARATION BY LE-TLC 164
5.3 COMPLEXATION GAS CHROMATOGRAPHY 165 5.4 LE-ELECTROMIGRATION
TECHNIQUES 165 5.4.1 SEPARATION BY CAPILLARY ZONE ELECTROPHORESIS (CZE)
165 5.4.2 SEPARATION BY MICELLAR ELECTROKINETIC CHROMATOGRAPHY (MEKC)
171 5.4.3 SEPARATION BY MICRO-CHANNEL CHIP ELECTROPHORESIS 172 5.4.4
SEPARATION BY CAPILLARY ELECTROCHROMATOGRAPHY (CEC) 172 LIST OF
ABBREVIATIONS 175 REFERENCES 176 6 ADVANCES IN SIMULATED MOVING BED
CHROMATOGRAPHIC SEPARATIONS 181 PEDRO S6 GOMES, MIRJANA MINCEVA, LUIS S.
PAIS, AND ALIRIO E. RODRIGUES 6.1 INTRODUCTION 181 6.2 MODELING
STRATEGIES 183 6.2.1 REAL SMB 183 6.2.1.1 DETAILED PARTICLE MODEL 184
6.1.2.1 LINEAR DRIVING FORCE APPROACH 186 6.2.2 EQUIVALENT TMB 186
6.2.2.1 DETAILED PARTICLE MODEL 187 6.2.2.2 LDF APPROACH 289 6.3
SIMULATION 189 6.3.1 NUMERICAL SOLUTION 189 6.3.2 CASE STUDY: OPERATING
CONDITIONS AND MODEL PARAMETERS 190 6.3.3 SIMULATIONS RESULTS 191
6.3.3.1 REAL SMB MODELS 191 6.3.3.2 EQUIVALENT TMB MODELS 194 6.4 NOVEL
SMB CONFIGURATIONS 195 6.4.1 VARICOL AND MULTIPLE FEED SMB 195 6.4.1.1
VARICOL 195 6.4.1.2 MULTIPLE (DISTRIBUTED) FEED 198 6.5 IMPROVEMENTS IN
OPERATION CONDITIONS EVALUATION (SEPARATION VOLUME METHOD} 200 6.6
CONCLUSIONS 201 REFERENCES 201 CONTENTS I IX 7 LESS COMMON APPLICATIONS
OF ENANTIOSELECTIVE HPLC USING THE SMB TECHNOLOGY IN THE PHARMACEUTICAL
INDUSTRY 203 STEFONIE ABEL AND MARKUSJUZA 7.1 INTRODUCTION - FROM AN
EMERGING TECHNOLOGY TO A CLASSICAL UNIT OPERATION 203 7.1.1 LESS COMMON
APPLICATIONS OF SMB TECHNOLOGY FOR CHIRAL SEPARATIONS 206 7.1.2 DESIGN
AND OPTIMIZATION OF OPERATING CONDITIONS FOR A CLASSICAL SMB SEPARATION
208 7.1.3 CHIRAL STATIONARY PHASES 211 7.2 UNBALANCED SEPARATIONS AND
MULTI-COMPONENT SEPARATIONS USING SMB 213 7.2.1 BINARY SEPARATIONS 214
7.2.1.1 CASE STUDY I: 1:1 VS. 10:1 AND 1:10 215 7.2.2 THREE-COMPONENT
SEPARATIONS 217 7.2.2.1 CASE STUDY II: THREE-COMPONENT SEPARATIONS WITH
TWO TARGETS 218 7.2.3 MULTI-COMPONENT SEPARATIONS VIA SMB 221 7.2.3.1
CASE STUDY III: MULTI-COMPONENT SEPARATION 221 7.2.4 GENERALIZED RULES
FOR OPTIMIZING UNBALANCED AND MULITCOMPONENT SEPARATIONS VIA SMB 223
7.2.4.1 DETECTING PROBLEMS 223 7.2.4.2 SOLVING PROBLEMS 225 7.3 UNUSUAL
ISOTHERMS AND ADSORPTION BEHAVIOR 225 7.3.1 LANGMUIR ADSORPTION ISOTHERM
226 7.3.2 NON-LANGMUIR ADSORPTION ISOTHERMS 227 7.3.2.1 PEAK SHAPE AND
FORM OF LINEAR AND ANTI-LANGMUIR ISOTHERMS 229 7.3-2.2 REGION OF
COMPLETE SEPARATION FOR AN ANTI-LANGMUIR ISOTHERM 230 7.3.3 CASE STUDIES
231 7.3.3.1 CASE STUDY IV: BOTH COMPOUNDS SHOW ANTI-LANGMUIRIAN BEHAVIOR
232 7.3.3.2 CASE STUDY V: ONE COMPOUND SHOWS ANTI-LANGMUIRIAN BEHAVIOR
234 7.3.4 GENERAL TRENDS FOR LOADING STUDIES AND ADSORPTION ISOTHERMS
237 7.4 APPLICATIONS OF VARIOUS COLUMN CONFIGURATIONS 237 7.4,1
SYMMETRICAL CONFIGURATIONS 237 7.4.1.1 CASE STUDY VI: COMPARING A
2-2-2-2 AND A 1-2-2-1 CONFIGURATION 240 7.4.1 ASYMMETRIC CONFIGURATIONS
241 7.5 APPLICATION OF SOLVENT GRADIENTS 243 7.5.1 SOLVENT GRADIENT SMB
244 7.5.1.1 CASE STUDY VII: PREPARATIVE-SCALE SMB APPLYING A REVERSED
SOLVENT GRADIENT 247 7.6 CHEMISTRY AND RACEMIZATION 251 7.6.1
RACEMIZATION 253 7.6.2 CASE STUDIES 257 X I CONTENTS 7.6.2.1 CASE STUDY
VIII: ASBAT INHIBITOR 257 7.6.2.2 CASE STUDY IX'. ANTIDEPRESSANT OXETINE
DERIVATIVES 258 7.6.2.3 CASE STUDY X: ZOLOFT, A SEROTONIN REUPTAKE
INHIBITOR 259 7.6.2.4 CASE STUDY XI: SYNTHESIS OF ENANTIOMERICALLY PURE
AMINES VIA SCHIFF BASES 262 7.6.2.5 CASE STUDY XII: SYNTHESIS OF COX-2
INHIBITORS 263 7.7 FUTURE DEVELOPMENTS 264 7-7.1 NON-HPLC
ENANTIOSELECTIVE SMB MODES 265 7.7.2 OPERATION MODES, MODELING SOFTWARE,
CONTROL OF SMB UNITS, AND STATIONARY PHASES 266 7.8 CONCLUSION 267
NOTATION 268 GREEK LETTERS 268 SUBSCRIPTS 268 ACKNOWLEDGMENTS 268
REFERENCES 269 3 ENANTIOMER SEPARATION BY CHIRAL CROWN ETHER STATIONARY
PHASES 275 MYUNG HO HYUN 8.1 INTRODUCTION 275 8.2 DEVELOPMENT OF CSPS
276 8.2.1 CSPS BASED ON CHIRAL CROWN ETHERS INCORPORATING A CHIRAL
L,L'-BINAPHTHYL UNIT 276 8.2.2 CSPS BASED ON CHIRAL CROWN ETHERS
INCORPORATING A TARTARIC ACID UNIT 277 8.2.3 CSPS BASED ON PHENOLIC
PSEUDO CHIRAL CROWN ETHERS 281 8.3 APPLICATIONS OF CSPS 282 8.3.1
RESOLUTION OF PRIMARY AMINO COMPOUNDS 282 8.3.2 RESOLUTION OF
NON-PRIMARY AMINO COMPOUNDS 285 8.4 COMPOSITION OF MOBILE PHASE 288
8.4.1 AQUEOUS MOBILE PHASE 288 8.4.1.1 ORGANIC MODIFIER IN AQUEOUS
MOBILE PHASE 288 8.4.1.2 ACIDIC MODIFIER IN AQUEOUS MOBILE PHASE 290
8.4.1.3 INORGANIC CATIONIC MODIFIER IN AQUEOUS MOBILE PHASE 293 8.4.2
NONAQUEOUS MOBILE PHASE 294 8.5 TEMPERATURE EFFECT 295 8.6 CONCLUSION
297 ACKNOWLEDGMENT 298 REFERENCES 298 CONTENTS XI 9 ENANTIOSELECTIVE
SEPARATION OF AMINO ACIDS AND HYDROXY ACIDS BY LIGAND EXCHANGE WITH
COPPER(LL) COMPLEXES IN HPLC (CHIRAL ELUENT) AND IN FAST SENSING SYSTEMS
301 ROSANGETA MARCHELTI, ROBERTO CARRADINI, GIANNI GOIAVERNA, ARNALDO
DOSSENA, FRANCESCO DALLAVALLE, AND STEFANO SFORZA 9.1 INTRODUCTION 301
9.2 ENANTIOMERIC SEPARATION OF AMINO ACIDS AND HYDROXY ACIDS WITH THE
CHIRAL SELECTORS ADDED TO THE MOBILE PHASE IN HPLC (CMPS) 303 9.2.1
BIDENTATE LIGANDS 303 9.2.1.1 ENANTIOMERIC SEPARATION OF FREE D,L-AMINO
ACIDS 303 9.2.1.2 ENANTIOMERIC SEPARATION OF D,L-DNS-AMINO ADDS 308
9.2.1.3 ENANTIOMERIC SEPARATION OF A-HYDROXY ACIDS AND DICARBOXYLIC
ACIDS 309 9.2.2 TERDENTATE LIGANDS 312 9.2.2.1 ENANTIOSEPARATION OF
UNMODIFIED AMINO ACIDS 312 9.2.2.2 ENANTIOSEPARATIO N OF DNS-AMINO ACIDS
314 9.2.3 TETRADENTATE LIGANDS 315 9.2.3.1 ENANTIOMERIC SEPARATION OF
UNMODIFIED AMINO ACIDS 316 9.2.3.2 CHIRAL SEPARATION OF DNS-AMINO ACIDS
318 9.3 DYNAMICALLY COATED STATIONARY PHASES 319 9.4 COMPARISON BETWEEN
ENANTIOMERIC SEPARATIONS OBTAINED WITH THE CHIRAL SELECTOR BOUND TO THE
STATIONARY PHASE OR ADDED TO THE ELUENT 320 9.5 MIXED
INCLUSION-LIGAND-EXCHANGE CHROMATOGRAPHY 325 9.6 LIGAND EXCHANGE IN FAST
SENSING SYSTEMS 327 ACKNOWLEDGMENT 329 REFERENCES 329 10 ENANTIOMER
SEPARATION BY CAPILLARY ELECTROPHORESIS 333 GERHARD K. E. SCRIBA 10.1
INTRODUCTION 333 10.2 MODES OF CAPILLARY ELECTROMIGRATION TECHNIQUES 334
10.3 THEORY OF ELECTROPHORETIC SEPARATIONS 334 10.3.1 BASICS OF
CAPILLARY ELECTROPHORESIS 334 10.3.2 CHIRAL SEPARATIONS 335 10.4
ENANTIOMER SEPARATIONS 337 10.4.1 INDIRECT CHIRAL SEPARATIONS 338 10.4.2
DIRECT CHIRAL SEPARATIONS 338 10.4.2.1 CYCLODEXTRINS 343 10.4.2.2
MACROCYDIC ANTIBIOTICS 346 10.4.2.3 CHIRAL CROWN ETHERS 349 10.4.2.4
CHIRAL UGAND EXCHANGE 350 10.4.2.5 CHIRAL ION-PAIR REAGENTS 350 10.4.2.6
CHIRAL SURFACTANTS 351 XII CONTENTS 10.4.2.7 MISCELLANEOUS CHIRAL
SELECTORS 353 10.5 APPLICATIONS 354 10.6 METHOD DEVELOPMENT AND
VALIDATION 358 10.7 MIGRATION MODELS 362 10.8 ENANTIOMER MIGRATION ORDER
364 10.9 FUTURE TRENDS 365 REFERENCES 366 11 COUNTER-CURRENT
CHROMATOGRAPHY IN THE SEPARATION OF ENANTIOMERS 369 EVA P6REZ AND
CRISTINA MINGUILLON 11.1 INTRODUCTION 369 11.2 INSTRUMENTATION 3 71 11.3
SOME THOUGHTS ON CCC ENANTIOSEPARATION 372 11.4 CHIRAL SELECTORS USED IN
CCC ENANTIOSEPARATIONS 375 11.4.1 CHIRAL RECOGNITION IN THE AQUEOUS
PHASE 375 11.4.2 CHIRAL RECOGNITION IN THE ORGANIC PHASE 380 11.5
PH-ZONE-REFINING CCC 387 11.6 SAMPLE RESOLUTION IN CCC 392 11.7
CONTINUOUS CPC 393 11.8 CONCLUSIONS AND FUTURE TRENDS 394
ACKNOWLEDGMENTS 394 REFERENCES 395 12 SEPARATION OF ENANTIOMERS USING
MOLECULARLY IMPRINTED POLYMERS 399 BORJE SELLERGREN 12.1 INTRODUCTION
399 12.2 FUNDAMENTAL STUDIES USING ENANTIOMERS AS MODEL TEMPLATES 401
12.3 USING FRONTAL ANALYSIS TO ELUCIDATE RETENTION MECHANISMS 406 12.4
APPROACHES TO BINDING SITE DESIGN 412 12.4.1 COMBINATORIAL AND
COMPUTATIONAL TECHNIQUES TO OPTIMIZING MICSPS 413 12.4.2 MICSPS BY
RATIONAL DESIGN 415 12.5 OTHER FORMATS: BEADS, MONOLITHS, AND FILMS 418
12.5.1 BEADS AND NANOPARTIDES 419 12.5.2 LAYERS AND FILMS 421 12.5.3
SUPERPOROUS MONOLITHS 425 12.5.4 HIERARCHICAL IMPRINTING TECHNIQUES 426
12.6 OTHER MATRICES FOR IMPRINTING OF ENANTIOMERS 426 12.7 CONCLUSIONS
429 REFERENCES 429 CONTENTS XIII 13 ENANTIOSELECTIVE BIOSENSORS
RAIUCA-LOANA STEFAN-VAN STADEN, JACOBUS FREDERICK VAN STADEN, AND HASSAN
Y, ABOUL-ENEIN 433 13.1 I NTRODUCTION 433 13.2 THE DESIGN OF
ENANTIOSELECTIVE ELECTROCHEMICAL BIOSENSORS 433 13.3 APPLICATIONS OF
ENANTIOSELECTIVE ANALYSIS 434 13.3.1 AMINO ACIDS 434 13.3.2
ANGIOTENSIN-CONVERTING ENZYME INHIBITORS 434 13.3.3 THYROID HORMONES 435
13.3.4 ALANINE 435 13.3.5 CARNITINE AND O-ACETYL-L-CARNITINE 436 13.3.6
LYSINE 436 13.3.7 METHOTREXATE 437 13.3.8 PIPECOLIC ACID 437 13.4
CONCLUSION 438 REFERENCES 438 14 CHIRAL ANALYSIS IN CAPILLARY
ELECTROCHROMATOGRAPHY (CEC) AND CEC COUPLED TO MASS SPECTROMETRY 441 JIE
ZHENG AND SHAHAB A, SHAMS'I 14.1 INTRODUCTION 441 14.2 CEC COLUMN
TECHNOLOGIES FOR CHIRAL SEPARATION 443 14.2.1 PACKED CAPILLARIES 443
14.2.2 OPEN-TUBULAR CAPILLARIES 445 14.2.3 MONOLITHIC CAPILLARIES 447
14.2.3.1 INORGANIC MONOLITH-BASED COLUMNS 447 14.2.3.2 ORGANIC POLYMERIC
MONOLITHIC COLUMNS 448 14.2.3.3 PARTICLE-LOADED MONOLITHIC COLUMNS 450
14.3 CHIRAL STATIONARY PHASES FOR CEC 45J 14.3.1 BRUSH-TYPE CSPS 453
14.3.2 CYCLODEXTRINS AND THEIR DERIVATIVES 456 14.3.3 MACROCYCLIC
GLYCOPEPTIDE-BONDED CSPS 460 14.3.4 POLYSACCHARIDE-BASED CSPS 466 14.3.5
PROTEIN-BASED CSPS 473 14.3.6 MOLECULAR IMPRINTING-BASED CSPS 475 14.3.7
LIGAND EXCHANGE-BASED CSPS 477 14.3.8 ION EXCHANGE-BASED CSPS 479 14.3.9
MISCELLANEOUS 483 14.4 CHIRAL CEC COUPLED TO MASS SPECTROMETRIC
DETECTION 485 14.4.1 CEC/MS INSTRUMENTATION AND COLUMN TECHNOLOGY 486
14.4.2 CHIRAL CEC/MS APPLICATIONS 491 14.5 CONCLUSIONS 499 LIST OF
ABBREVIATIONS 500 REFERENCES 50I XIV I CONTENTS 15 CHIRAL ANALYSIS USING
POLYMERIC SURFACTANTS IN MICELLAR ELECTROKINETIC CHROMATOGRAPHY (MEKC)
AND MEKC COUPLED TO MASS SPECTROMETRY 505 SYED A. A. RIZVI AND SHAHAB A.
SHAMSI 15.1 INTRODUCTION 505 15.2 CHIRAL ANIONIC SURFACTANTS 509 15.2.1
AMINO ACID-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS WITH AMIDE LINKAGE
509 15.2.2 PEPTIDE-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS WITH AMIDE
LINKAGE 525 15.2.3 AMINO ACID-BASED POLYMERIC CHIRAL ANIONIC SURFACTANTS
WITH CARBAMATE LINKAGE 537 15.3 CHIRAL CATIONIC SURFACTANTS 544 15.3.1
SINGLE AMINO ACID-BASED CATIONIC SURFACTANTS WITH AMIDE LINKAGE 544 15.4
COUPLING OF MEKC TO MASS SPECTROMETRY USING POLYMERIC SURFACTANTS 545
15.4.1 MEKC/MS METHOD DEVELOPMENT 547 15.4.2 MEKC/MS OF
()-L,L'-BINAPHTHOL (BOH) 548 15.4.3 MEKC/MS OF ^-BLOCKERS 550 15.4.4
MEKC/MS OF BENZODIAZEPINES AND BENZOXAZOCINE 555 15.5 CONCLUSIONS 556
ACKNOWLEDGMENT 557 LIST OF ABBREVIATIONS 557 REFERENCES 559 16
POLARIMETER CHIRAL DETECTORS IN ENANTIOSEPARATIONS 561 GARY W. YANIK
16.1 INTRODUCTION 561 16.2 THEORY OF OPERATION 562 16.3 COMPARISON WITH
UV AND CD DETECTION 565 16.4 USEFUL DEFINITIONS 565 16.4.1 CHEMICAL
PURITY (CP) 565 16.4.2 ENANTIOMERIC PURITY (EP) 566 16.4.3 ENANTIOMERIC
EXCESS {EE) 566 16.4.4 SPECIFIC ROTATION \SR) 566 16.5 AUTOMATION OF
METHOD DEVELOPMENT AND PREPARATIVE PURIFICATIONS 566 16.6 METHOD
DEVELOPMENT 568 16.7 PREPARATIVE PURIFICATIONS 569 16.8 ANALYTES 572
16.8.1 SMALL MOLECULE PHARMACEUTICAL CANDIDATES 572 16.8.2 ANTIBIOTICS
AND SUGARS: COMPOUNDS WITHOUT CHROMOPHORES 574 16.8.3 AMINO ACIDS 575
16.8.4 NATURAL PRODUCTS 575 CONTENTS XV 16.8.5 FOODS, FLAVORS, AND
FRAGRANCES 575 16.8.6 FERTILIZERS AND PESTICIDES 576 16.9 APPLICATIONS
577 16.9.1 ANALYSIS AND QA/QC 577 16.9.2 EXAMPLE: QA/QC OF ANTIBIOTIC
RESIDUES IN MILK - GENTAMICIN 577 16.9.3 HPLC/SFC METHOD DEVELOPMENT 580
16.9.4 HPLC/SFC PREPARATIVE PURIFICATION - FRACTION COLLECTION 580
16.9.5 PROCESS MONITORING 581 16.10 SUMMARY AND CONCLUSION 584
REFERENCES 584 17 PREPARATIVE CHIRAL CHROMATOGRAPHY - A POWERFUL AND
EFFICIENT TOOL IN DRUG DISCOVERY 585 SHAIINI ANCFERSSON 17.1
INTRODUCTION 585 17.2 CHIRAL CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERS
586 17.2.1 SELECTING THE CHIRAL STATIONARY PHASE 586 17.3 CHIRAL
PREPARATIVE CHROMATOGRAPHY PROCESS 588 17.3.1 COLUMN SCREEN AND
OPTIMIZATION 588 17.3.2 PREPARATIVE CHROMATOGRAPHY 590 17.3.2.1 CHOICE
OF THE CHROMATOGRAPHY MODE 590 17.3.2.2 LOADABILITY 593 17.3.2.3
SOLUBILITY 592 17'.4 EXAMPLES OF PREPARATIVE SEPARATION OF ENANTIOMERS
593 17.4.1 RESOLUTION OF DNZ-/?-PHENYLALANINE ISOMERS 593 17.4.2
RESOLUTION OF A CHIRAL ACID IN LATE-STAGE DISCOVERY PHASE 595 17.5
ANALYSIS AND CHIROPTICAL CHARACTERIZATION OF THE ISOLATED ENANTIOMERS
598 17.6 CONDUSIONS 598 REFERENCES 599 SUBJECT INDEX 601 |
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| any_adam_object_boolean | 1 |
| building | Verbundindex |
| bvnumber | BV021784576 |
| callnumber-first | Q - Science |
| callnumber-label | QP517 |
| callnumber-raw | QP517.C57 |
| callnumber-search | QP517.C57 |
| callnumber-sort | QP 3517 C57 |
| callnumber-subject | QP - Physiology |
| classification_rvk | VG 7200 VG 7500 WC 3480 |
| classification_tum | CHE 232f CHE 615f |
| ctrlnum | (OCoLC)76797501 (DE-599)BVBBV021784576 |
| dewey-full | 543.84 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 543 - Analytical chemistry |
| dewey-raw | 543.84 |
| dewey-search | 543.84 |
| dewey-sort | 3543.84 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Biologie Chemie Medizin |
| discipline_str_mv | Chemie / Pharmazie Biologie Chemie Medizin |
| edition | 3., completely rev. and updated ed. |
| format | Book |
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| id | DE-604.BV021784576 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:42:38Z |
| indexdate | 2024-07-09T20:44:01Z |
| institution | BVB |
| isbn | 9783527315093 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014997308 |
| oclc_num | 76797501 |
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| owner | DE-29T DE-703 DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-11 |
| owner_facet | DE-29T DE-703 DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-11 |
| physical | XXII, 618 S. Ill., graph. Darst. |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Chiral separation techniques a practical approach ed. by Ganapathy Subramanian 3., completely rev. and updated ed. Weinheim WILEY-VCH 2007 XXII, 618 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Chirality Industrial applications Enantiomers Separation Liquid chromatography Trennverfahren (DE-588)4078395-9 gnd rswk-swf Flüssigkeitschromatographie (DE-588)4017622-8 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf Enantiomerentrennung (DE-588)4135272-5 gnd rswk-swf Enantiomerentrennung (DE-588)4135272-5 s Trennverfahren (DE-588)4078395-9 s DE-604 Chirale Verbindungen (DE-588)4348527-3 s Flüssigkeitschromatographie (DE-588)4017622-8 s 1\p DE-604 2\p DE-604 Subramanian, Ganapathy Sonstige oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2804051&prov=M&dok_var=1&dok_ext=htm Inhaltstext Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014997308&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Klappentext GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014997308&sequence=000003&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Chiral separation techniques a practical approach Chirality Industrial applications Enantiomers Separation Liquid chromatography Trennverfahren (DE-588)4078395-9 gnd Flüssigkeitschromatographie (DE-588)4017622-8 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Enantiomerentrennung (DE-588)4135272-5 gnd |
| subject_GND | (DE-588)4078395-9 (DE-588)4017622-8 (DE-588)4348527-3 (DE-588)4135272-5 |
| title | Chiral separation techniques a practical approach |
| title_auth | Chiral separation techniques a practical approach |
| title_exact_search | Chiral separation techniques a practical approach |
| title_exact_search_txtP | Chiral separation techniques a practical approach |
| title_full | Chiral separation techniques a practical approach ed. by Ganapathy Subramanian |
| title_fullStr | Chiral separation techniques a practical approach ed. by Ganapathy Subramanian |
| title_full_unstemmed | Chiral separation techniques a practical approach ed. by Ganapathy Subramanian |
| title_short | Chiral separation techniques |
| title_sort | chiral separation techniques a practical approach |
| title_sub | a practical approach |
| topic | Chirality Industrial applications Enantiomers Separation Liquid chromatography Trennverfahren (DE-588)4078395-9 gnd Flüssigkeitschromatographie (DE-588)4017622-8 gnd Chirale Verbindungen (DE-588)4348527-3 gnd Enantiomerentrennung (DE-588)4135272-5 gnd |
| topic_facet | Chirality Industrial applications Enantiomers Separation Liquid chromatography Trennverfahren Flüssigkeitschromatographie Chirale Verbindungen Enantiomerentrennung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=2804051&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014997308&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014997308&sequence=000003&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
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