Peptides: chemistry and biology
Gespeichert in:
| Späterer Titel: | Sewald, Norbert Peptides |
|---|---|
| Hauptverfasser: | , |
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2002
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXXIV, 562 S. Ill., graph. Darst. |
| ISBN: | 3527304053 |
Internformat
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Datensatz im Suchindex
| _version_ | 1804129229509492736 |
|---|---|
| adam_text | NORBERT SEWALD AND HANS-DIETER JAKUBKE
PEPTIDES: CHEMISTRY AND BIOLOGY
WILEY-VCH
CONTENTS
PREFACE XI
ABBREVIATIONS XIII
1 INTRODUCTION AND BACKGROUND 1
2 FUNDAMENTAL CHEMICAL AND STRUCTURAL PRINCIPLES 5
2.1 DEFINITIONS AND MAIN CONFORMATIONAL FEATURES OF THE PEPTIDE BOND 5
2.2 BUILDING BLOCKS, CLASSIFICATION, AND NOMENCLATURE 7
2.3 ANALYSIS OF THE COVALENT STRUCTURE OF PEPTIDES AND PROTEINS 11
2.3.1 SEPARATION AND PURIFICATION 12
2.3.1.1 SEPARATION PRINCIPLES 12
2.3.1.2 PURIFICATION TECHNIQUES 16
2.3.1.3 STABILITY PROBLEMS 18
2.3.1.4 EVALUATION OF HOMOGENEITY 19
2.3.2 PRIMARY STRUCTURE DETERMINATION 20
2.3.2.1 END GROUP ANALYSIS 21
2.3.2.2 CLEAVAGE OF DISULFIDE BONDS 23
2.3.2.3 ANALYSIS OF AMINO ACID COMPOSITION 24
2.3.2.4 SELECTIVE METHODS OF CLEAVING PEPTIDE BONDS 25
2.3.2.5 N-TERMINAL SEQUENCE ANALYSIS (EDMAN DEGRADATION) 27
2.3.2.6 C-TERMINAL SEQUENCE ANALYSIS 29
2.3.2.7 MASS SPECTROMETRY 30
2.3.2.8 PEPTIDE LADDER SEQUENCING 32
2.3.2.9 ASSIGNMENT OF DISULFIDE BONDS AND PEPTIDE FRAGMENT ORDERING 33
2.3.2.10 LOCATION OF POST-TRANSLATIONAL MODIFICATIONS AND BOUND
COFACTORS 35
2.4 THREE-DIMENSIONAL STRUCTURE 36
2.4.1 SECONDARY STRUCTURE 36
2.4.1.1 HELIX 37
2.4.1.2 0-SHEET 38
2.4.1.3 TURNS 39
2.4.1.4 AMPHIPHILIC STRUCTURES 41
2.4.2 TERTIARY STRUCTURE 43
2.4.2.1 STRUCTURE PREDICTION 46
VI CONTENTS
2.5 METHODS OF STRUCTURAL ANALYSIS 47
2.5.1 CIRCULAR DICHROISM 48
2.5.2 INFRARED SPECTROSCOPY 49
2.5.3 NMR SPECTROSCOPY 50
2.5.4 X-RAY CRYSTALLOGRAPHY 52
2.5.5 UV FLUORESCENCE SPECTROSCOPY 54
2.6 REFERENCES 55
3 BIOLOGICALLY ACTIVE PEPTIDES 61
3.1 OCCURRENCE AND BIOLOGICAL ROLES 61
3.2 BIOSYNTHESIS 73
3.2.1 RIBOSOMAL SYNTHESIS 73
3.2.2 POST-TRANSLATIONAL MODIFICATION 76
3.2.2.1 ENZYMATIC CLEAVAGE OF PEPTIDE BONDS 76
3.2.2.2 HYDROXYLATION 78
3.2.2.3 CARBOXYLATION 78
3.2.2.4 GLYCOSYLATION 78
3.2.2.5 AMIDATION 83
3.2.2.6 PHOSPHORYLATION 83
3.2.2.7 LIPIDATION 85
3.2.2.8 PYROGLUTAMYL FORMATION 86
3.2.2.9 SULFATATION 87
3.2.3 NONRIBOSOMAL SYNTHESIS 88
3.3 SELECTED BIOACTIVE PEPTIDE FAMILIES 90
3.3.1 PEPTIDE AND PROTEIN HORMONES 90
3.3.1.1 LIBERINS AND STATINS 92
3.3.1.2 PITUITARY HORMONES 96
3.3.1.3 NEUROHYPOPHYSEAL HORMONES 98
3.3.1.4 GASTROINTESTINAL HORMONES 99
3.3.1.5 PANCREATIC ISLET HORMONES 100
3.3.1.6 FURTHER PHYSIOLOGICALLY RELEVANT PEPTIDE HORMONES 103
3.3.2 NEUROPEPTIDES 107
3.3.2.1 OPIOID PEPTIDES 109
3.3.2.2 TACHYKININS 114
3.3.2.3 FURTHER SELECTED NEUROACTIVE PEPTIDES 116
3.3.3 PEPTIDE ANTIBIOTICS 119
3.3.3.1 NONRIBOSOMALLY SYNTHESIZED PEPTIDE ANTIBIOTICS 119
3.3.3.2 RIBOSOMALLY SYNTHESIZED PEPTIDE ANTIBIOTICS 124
3.3.4 PEPTIDE TOXINS 126
3.4 REFERENCES 130
4 PEPTIDE SYNTHESIS 135
4.1 PRINCIPLES AND OBJECTIVES 135
4.1.1 MAIN TARGETS OF PEPTIDE SYNTHESIS 135
4.1.1.1 CONFIRMATION OF SUGGESTED PRIMARY STRUCTURES 135
CONTENTS VII
4.1.1.2 DESIGN OF BIOACTIVE PEPTIDE DRUGS 136
4.1.1.3 PREPARATION OF PHARMACOLOGICALLY ACTIVE PEPTIDES AND PROTEINS
137
4.1.1.4 SYNTHESIS OF MODEL PEPTIDES 138
4.1.2 BASIC PRINCIPLES OF PEPTIDE BOND FORMATION 139
4.2 PROTECTION OF FUNCTIONAL GROUPS 142
4.2.1 N
A
-AMINO PROTECTION 143
4.2.1.1 ALKOXYCARBONYL-TYPE (URETHANE-TYPE) PROTECTING GROUPS 143
4.2.1.2 CARBOXAMIDE-TYPE PROTECTING GROUPS 152
4.2.1.3 SULFONAMIDE AND SULFENAMIDE-TYPE PROTECTING GROUPS 152
4.2.1.4 ALKYL-TYPE PROTECTING GROUPS 153
4.2.2 C
A
-CARBOXY PROTECTION 154
4.2.2.1 ESTERS 155
4.2.2.2 AMIDES AND HYDRAZIDES 157
4.2.3 C-TERMINAL AND BACKBONE N
A
-CARBOXAMIDE PROTECTION 160
4.2A SIDE-CHAIN PROTECTION 162
4.2.4.1 GUANIDINO PROTECTION 162
4.2.4.2 CO-AMINO PROTECTION 165
4.2.4.3 CO-CARBOXY PROTECTION 166
4.2.4.4 THIOL PROTECTION 168
4.2.4.5 IMIDAZOLE PROTECTION 171
4.2.4.6 HYDROXY PROTECTION 174
4.2.4.7 THIOETHER PROTECTION 176
4.2.4.8 INDOLE PROTECTION 177
4.2.4.9 CO-AMIDE PROTECTION 178
4.2.5 ENZYME-LABILE PROTECTING GROUPS 180
4.2.5.1 ENZYME-LABILE N
A
-AMINO PROTECTION 181
4.2.5.2 ENZYME-LABILE C
A
-CARBOXY PROTECTION AND ENZYME-LABILE LINKER
MOIETIES 182
4.2.6 PROTECTING GROUP COMPATIBILITY 184
4.3 PEPTIDE BOND FORMATION 184
4.3.1 ACYL AZIDES 185
4.3.2 ANHYDRIDES 186
4.3.2.1 MIXED ANHYDRIDES 187
4.3.2.2 SYMMETRICAL ANHYDRIDES 189
4.3.2.3 N-CARBOXY ANHYDRIDES 190
4.3.3 CARBODIIMIDES 191
4.3.4 ACTIVE ESTERS 195
4.3.5 ACYL HALIDES 200
4.3.6 PHOSPHONIUM REAGENTS 201
4.3.7 URONIUM REAGENTS 202
4.3.8 FURTHER SPECIAL METHODS 204
4.4 RACEMIZATION DURING SYNTHESIS 205
4.4.1 DIRECT ENOLIZATION 205
4.4.2 5(4H)-OXAZOLONE MECHANISM 205
4.4.3 RACEMIZATION TESTS: STEREOCHEMICAL PRODUCT ANALYSIS 208
VIII CONTENTS
4.5 SOLID-PHASE PEPTIDE SYNTHESIS (SPPS) 209
4.5.1 SOLID SUPPORTS AND LINKER SYSTEMS 212
4.5.2 SAFETY-CATCH LINKERS 220
4.5.3 PROTECTION SCHEMES 224
4.5.3.1 BOC/BZL-PROTECTING GROUPS SCHEME (MERRIFIELD TACTICS) 224
4.5.3.2 FMOC/TBU-PROTECTING GROUPS SCHEME (SHEPPARD TACTICS) 225
4.5.3.3 THREE- AND MORE-DIMENSIONAL ORTHOGONALITY 227
4.5.4 CHAIN ELONGATION 227
4.5.4.1 COUPLING METHODS 227
4.5.4.2 UNDESIRED PROBLEMS DURING ELONGATION 228
4.5.4.3 DIFFICULT SEQUENCES 230
4.5.4.4 ON-RESIN MONITORING 232
4.5.5 AUTOMATION OF THE PROCESS 232
4.5.6 SPECIAL METHODS 233
4.5.7 PEPTIDE CLEAVAGE FROM THE RESIN 235
4.5.7.1 ACIDOLYTIC METHODS 235
4.5.7.2 SIDE REACTIONS 236
4.5.7.3 ADVANTAGES AND DISADVANTAGES OF THE BOC/BZL AND FMOC/TBU
SCHEMES 237
4.5.8 EXAMPLES OF SYNTHESES BY LINEAR SPPS 237
4.6 BIOCHEMICAL SYNTHESIS 238
4.6.1 RECOMBINANT DNA TECHNIQUES 239
4.6.1.1 PRINCIPLES OF DNA TECHNOLOGY 239
4.6.1.2 EXAMPLES OF SYNTHESIS BY GENETIC ENGINEERING 243
4.6.1.3 CELL-FREE TRANSLATION SYSTEMS 244
4.6.2 ENZYMATIC PEPTIDE SYNTHESIS 247
4.6.2.1 INTRODUCTION 247
4.6.2.2 APPROACHES TO ENZYMATIC SYNTHESIS 248
4.6.2.3 MANIPULATIONS TO SUPPRESS COMPETITIVE REACTIONS 250
4.6.2.4 IRREVERSIBLE C-N LIGATIONS BY MIMICKING ENZYME SPECIFICITY 251
4.6.3 ANTIBODY-CATALYZED PEPTIDE BOND FORMATION 253
4.7 REFERENCES 256
5 SYNTHESIS CONCEPTS FOR PEPTIDES AND PROTEINS 269
5.1 STRATEGY AND TACTICS 269
5.1.1 LINEAR OR STEPWISE SYNTHESIS 269
5.1.2 SEGMENT CONDENSATION OR CONVERGENT SYNTHESIS 272
5.1.3 TACTICAL CONSIDERATIONS 273
5.1.3.1 SELECTED PROTECTING GROUP SCHEMES 273
5.1.3.2 , PREFERRED COUPLING TECHNIQUES 276
5.2 SYNTHESIS IN SOLUTION 277
5.2.1 - CONVERGENT SYNTHESIS OF MAXIMALLY PROTECTED SEGMENTS 277
5.2.1.1 THE SAKAKIBARA APPROACH TO PROTEIN SYNTHESIS 278
5.2.1.2 CONDENSATION OF LIPOPHILIC SEGMENTS 280
5.2.2 CONVERGENT SYNTHESIS OF MINIMALLY PROTECTED SEGMENTS 282
CONTENTS IX
5.2.2.1 CHEMICAL APPROACHES 282
5.2.2.2 ENZYMATIC APPROACHES 284
5.3 OPTIMIZED STRATEGIES ON POLYMERIC SUPPORT 286
5.3.1 STEPWISE SPPS 286
5.3.2 CONVERGENT SPPS 288
5.3.2.1 SOLID-PHASE SYNTHESIS OF PROTECTED SEGMENTS 289
5.3.2.2 SOLID SUPPORT-MEDIATED SEGMENT CONDENSATION 290
5.3.3 PHASE CHANGE SYNTHESIS 292
5.3.4 SOLUBLE-HANDLE APPROACHES 293
5.3.4.1 PICOLYL ESTER METHOD 293
5.3.4.2 LIQUID-PHASE METHOD 293
5.4 LIGATION OF UNPROTECTED PEPTIDE SEGMENTS 294
5.4.1 BACKBONE-ENGINEERED LIGATION 295
5.4.2 PRIOR CAPTURE-MEDIATED LIGATION 297
5.4.2.1 TEMPLATE-MEDIATED LIGATION 297
5.4.2.2 NATIVE CHEMICAL LIGATION 298
5.4.3 BIOCHEMICAL PROTEIN LIGATION 304
5.5 REFERENCES 306
6 SYNTHESIS OF SPECIAL PEPTIDES AND PEPTIDE CONJUGATES 311
6.1 CYCLOPEPTIDES 311
6.1.1 BACKBONE CYCLIZATION (HEAD-TO-TAIL CYDIZATION) 313
6.1.2 SIDE CHAIN-TO-HEAD AND TAIL-TO-SIDE CHAIN CYDIZATIONS 319
6.1.3 SIDE CHAIN-TO-SIDE CHAIN CYDIZATIONS 319
6.2 CYSTINE PEPTIDES 320
6.3 . GLYCOPEPTIDES 322
6.4 PHOSPHOPEPTIDES 329
6.5 LIPOPEPTIDES 331 . .
6.6 SULFATED PEPTIDES 333
6.7 REFERENCES 334
7 PEPTIDE AND PROTEIN DESIGN, PSEUDOPEPTIDES, AND PEPTIDOMIMETICS 339
7.1 PEPTIDE DESIGN 340
7.2 MODIFIED PEPTIDES 345
7.2.1 SIDE-CHAIN MODIFICATION 345
7.2.2 BACKBONE MODIFICATION 348
7.2.3 COMBINED MODIFICATION (GLOBAL RESTRICTION) APPROACHES 350
7.2.4 MODIFICATION BY SECONDARY STRUCTURE MIMETICS 352
7.2.5 TRANSITION STATE INHIBITORS 353
7.3 PEPTIDOMIMETICS 354
7.4 PSEUDOBIOPOLYMERS 357
7.4.1 PEPTOIDS 358
7.4.2 PEPTIDE NUCLEIC ACIDS (PNA) 360
7.4.3 P-PEPTIDES, HYDRAZINO PEPTIDES, AMINOXY PEPTIDES,
AND OLIGOSULFONAMIDES 361
CONTENTS
7.4.4 OLIGOCARBAMATES 362
7.4.5 OLIGOPYRROLINONES 363
7.5 MACROPEPTIDES AND DE-NOVO DESIGN OF PEPTIDES AND PROTEINS 364
7.5.1 PROTEIN DESIGN 364
7.5.2 PEPTIDE DENDRIMERS 369
7.5.3 PEPTIDE POLYMERS 371
7.6 REFERENCES 372
8 COMBINATORIAL PEPTIDE SYNTHESIS 379
8.1 PARALLEL SYNTHESIS 382
8.1.1 SYNTHESIS IN TEABAGS 383
8.1.2 SYNTHESIS ON POLYETHYLENE PINS (MULTIPIN SYNTHESIS) 384
8.1.3 PARALLEL SYNTHESIS OF SINGLE COMPOUNDS ON CELLULOSE
OR POLYMER STRIPS 385
8.1.4 LIGHT-DIRECTED, SPATIALLY ADDRESSABLE PARALLEL SYNTHESIS 387
8.1.5 LIQUID-PHASE SYNTHESIS USING SOLUBLE POLYMERIC SUPPORT 388
8.2 SYNTHESIS OF MIXTURES 389
8.2.1 REAGENT MIXTURE METHOD 389
8.2.2 SPLIT AND COMBINE METHOD 390
8.2.3 ENCODING METHODS 392
8.2.4 PEPTIDE LIBRARY DECONVOLUTION 396
8.2.5 BIOLOGICAL METHODS FOR THE SYNTHESIS OF PEPTIDE LIBRARIES 397
8.3 REFERENCES 399
9 APPLICATION OF PEPTIDES AND PROTEINS 403
9.1 PROTEIN PHARMACEUTICALS 403
9.1.1 IMPORTANCE AND SOURCES 403
9.1.2 ENDOGENOUS PHARMACEUTICAL PROTEINS 404
9.1.3 ENGINEERING OF THERAPEUTIC PROTEINS 406
9.1.3.1 PEPTIDE-BASED VACCINES 407
9.1.3.2 MONOCLONAL ANTIBODIES 407
9.1.3.3 PROTEIN PHARMACEUTICALS WITH VARIOUS FUNCTIONS 409
9.1.3.4 FUTURE PERSPECTIVES 410
9.2 LARGE-SCALE PEPTIDE SYNTHESIS 412
9.3 PEPTIDE PHARMACEUTICALS 416
9.3.1 PEPTIDE DRUGS AND DRUG CANDIDATES 416
9.3.2 PEPTIDE DRUG DELIVERY SYSTEMS 419
9.3.3 PEPTIDES AS TOOLS IN DRUG DISCOVERY 421
9.3.3.1 PEPTIDES TARGETED TO FUNCTIONAL SITES OF PROTEINS 422
9.3.3.2 PEPTIDES USED IN TARGET VALIDATION 423
9.3.3.3 PEPTIDES AS SURROGATE LIGANDS FOR HTS 424
9.4 REFERENCES 425
GLOSSARY 429
INDEX 545
|
| any_adam_object | 1 |
| author | Sewald, Norbert 1961- Jakubke, Hans-Dieter 1933- |
| author_GND | (DE-588)120773473 (DE-588)1056797495 |
| author_facet | Sewald, Norbert 1961- Jakubke, Hans-Dieter 1933- |
| author_role | aut aut |
| author_sort | Sewald, Norbert 1961- |
| author_variant | n s ns h d j hdj |
| building | Verbundindex |
| bvnumber | BV014331025 |
| classification_rvk | VK 8560 WD 5250 |
| classification_tum | CHE 820f |
| ctrlnum | (OCoLC)248640002 (DE-599)BVBBV014331025 |
| dewey-full | 547.756 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.756 |
| dewey-search | 547.756 |
| dewey-sort | 3547.756 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Biologie Chemie |
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| id | DE-604.BV014331025 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T19:01:49Z |
| institution | BVB |
| isbn | 3527304053 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009831507 |
| oclc_num | 248640002 |
| open_access_boolean | |
| owner | DE-703 DE-355 DE-BY-UBR DE-20 DE-19 DE-BY-UBM DE-1046 DE-91G DE-BY-TUM DE-29T DE-526 DE-11 DE-188 |
| owner_facet | DE-703 DE-355 DE-BY-UBR DE-20 DE-19 DE-BY-UBM DE-1046 DE-91G DE-BY-TUM DE-29T DE-526 DE-11 DE-188 |
| physical | XXXIV, 562 S. Ill., graph. Darst. |
| publishDate | 2002 |
| publishDateSearch | 2002 |
| publishDateSort | 2002 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Sewald, Norbert 1961- Verfasser (DE-588)120773473 aut Peptides chemistry and biology Norbert Sewald and Hans-Dieter Jakubke Weinheim Wiley-VCH 2002 XXXIV, 562 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Peptide Biologie (DE-588)4006851-1 gnd rswk-swf Chemie (DE-588)4009816-3 gnd rswk-swf Peptide (DE-588)4045125-2 gnd rswk-swf Peptide (DE-588)4045125-2 s Chemie (DE-588)4009816-3 s 1\p DE-604 Biologie (DE-588)4006851-1 s 2\p DE-604 Jakubke, Hans-Dieter 1933- Verfasser (DE-588)1056797495 aut 2. Aufl. u.d.T. Sewald, Norbert Peptides (DE-604)BV035386905 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009831507&sequence=000001&line_number=0001&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 | Sewald, Norbert 1961- Jakubke, Hans-Dieter 1933- Peptides chemistry and biology Peptide Biologie (DE-588)4006851-1 gnd Chemie (DE-588)4009816-3 gnd Peptide (DE-588)4045125-2 gnd |
| subject_GND | (DE-588)4006851-1 (DE-588)4009816-3 (DE-588)4045125-2 |
| title | Peptides chemistry and biology |
| title_auth | Peptides chemistry and biology |
| title_exact_search | Peptides chemistry and biology |
| title_full | Peptides chemistry and biology Norbert Sewald and Hans-Dieter Jakubke |
| title_fullStr | Peptides chemistry and biology Norbert Sewald and Hans-Dieter Jakubke |
| title_full_unstemmed | Peptides chemistry and biology Norbert Sewald and Hans-Dieter Jakubke |
| title_new | Sewald, Norbert Peptides |
| title_short | Peptides |
| title_sort | peptides chemistry and biology |
| title_sub | chemistry and biology |
| topic | Peptide Biologie (DE-588)4006851-1 gnd Chemie (DE-588)4009816-3 gnd Peptide (DE-588)4045125-2 gnd |
| topic_facet | Peptide Biologie Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009831507&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT sewaldnorbert peptideschemistryandbiology AT jakubkehansdieter peptideschemistryandbiology |