Biochemistry of peptide antibiotics: recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides
Saved in:
| Format: | Book |
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| Language: | English |
| Published: |
Berlin ; New York
<<de>> Gruyter
1990
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIV, 522 S. Ill. |
| ISBN: | 3110119285 0899255515 |
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| 245 | 1 | 0 | |a Biochemistry of peptide antibiotics |b recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides |c ed. Horst Kleinkauf ; Hans von Döhren |
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Record in the Search Index
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| adam_text | BIOCHEMISTRY OF PEPTIDE ANTIBIOTICS RECENT ADVANCES IN THE BIOTECHNOLOGY
OF JS-LACTAMS AND MICROBIAL BIOACTIVE PEPTIDES EDITORS HORST KLEINKAUF *
HANS VON DOHREN W DE G WALTER DE GRUYTER BERLIN * NEW YORK 1990 CONTENTS
CHAPTER 1 BIOACTIVE PEPTIDES * RECENT ADVANCES AND TRENDS HORST
KLEINKAUF AND HANS VON DOHREN 1. PEPTIDES OF RIBOSOMAL ORIGIN 2 1.1
PROTEIN ANTIBIOTICS . 2 1.2 PEPTIDE HORMONES AND NEUROPEPTIDES 2 1.3
LANTIBIOTICS 4 2. ENZYMATICALLY FORMED PEPTIDES AND POLYPEPTIDES 6 2.1
SINGLE ENZYMES OR MULTIENZYME 7 2.2 SIZE OF PEPTIDE FORMED 7 2.3
STRUCTURE OF MULTIENZYMES 8 2.4 THE THIOTEMPLATE MECHANISM 8 2.5 ENZYMIC
SYNTHESIS OF PEPTIDES 12 3. GENETICS OF PEPTIDE SYNTHETASES 14 3.1
SIDEROPHORES 14 3.2 BACILLUS PEPTIDES: GRAMICIDIN S, TYROCIDINE,
BACITRACIN 16 3.3 GENES INVOLVED IN /MACTAM-BIOSYNTHESIS 17 3.4 MORE
UNIFIED APPROACHES TO BIOSYNTHETIC PATHWAYS 18 4. NEW AND OLD SOURCES OF
PEPTIDES 20 5. CONCLUSIONS 23 REFERENCES 26 CHAPTER 2 * GRAMICIDIN S
SYNTHETASE JOACHIM VATER 1. INTRODUCTION 33 2. PURIFICATION OF
GRAMICIDIN S SYNTHETASE 34 3. PHYSICAL AND BIOCHEMICAL PROPERTIES OF
GRAMICIDIN S SYNTHETASE 36 4. REACTION MECHANISM OF THE BIOSYNTHESIS OF
GRAMICIDIN S AND PRODUCT PATTERNS OF GRAMICIDIN S SYNTHETASE 37 5.
REACTION CENTERS FOR SUBSTRATE ACTIVATION 40 6. INHIBITOR STUDIES 43 7.
STRUCTURAL ASPECTS 46 8. INVESIGATION OF GRAMICIDIN S NEGATIVE MUTANTS
49 9. PROSPECTS 50 REFERENCES 51 VIII CONTENTS CHAPTER 3 FORMATION OF
TV-METHYLATED PEPTIDE BONDS IN PEPTIDES AND PEPTIDOLS ANDREAS BILLICH
AND RAINER ZOCHER 1. INTRODUCTION 57 2. OCCURRENCE OF TV-METHYLATED
PEPTIDE BONDS 57 3. BIOSYNTHESIS OF TV-METHYLATED PEPTIDES 60 4. THE
TV-METHYLTRANSFERASE FUNCTION OF ENNIATIN SYNTHETASE 62 4.1
TV-METHYLATION OF ENZYME-BOUND AMINO ACIDS 63 4.2 KINETIC PROPERTIES OF
THE TV-METHYLTRANSFERASE FUNCTION 64 4.3 INHIBITION STUDIES OF THE
TV-METHYLTRANSFERASE FUNCTION 64 4.4 PHOTOAFFMITY LABELING OF ENNIATIN
SYNTHETASE 68 4.5 MONOCLONAL ANTIBODIES TO ENNIATIN SYNTHETASE 70 5. THE
TV-METHYLTRANSFERASE FUNCTION OF OTHER PEPTIDES SYNTHETASES 72 5.1
BEAUVERICIN SYNTHETASE 72 5.2 CYCLOSPORIN SYNTHETASE 73 5.3 ACTINOMYCIN
SYNTHETASES 75 6. CONCLUSIONS 76 REFERENCES 77 CHAPTER 4 PEPTIDE BOND
SYNTHESIS BY ENZYME-CATALYZED ACYL-TRANSFER VOLKER KASCHE AND GILNTHER
MICHAELIS 1. INTRODUCTION 81 2. MECHANISM OF THE KINETICALLY CONTROLLED
PEPTIDE SYNTHESIS 83 3. MAXIMUM YIELDS IN THE KINETICALLY CONTROLLED
PEPTIDE SYNTHESIS 85 4. SELECTING THE OPTIMAL ENZYME 89 5. YIELD
CONTROLLING FACTORS IN THE SYNTHESIS OF A PEPTIDE BOND WITH ONE ENZYME
94 5.1 PROTECTION OF THE P I CARBOXYL GROUP; STEREOSPECIFITY 94 5.2 PH
VALUE 95 5.3 TEMPERATURE 96 5.4 IONIC STRENGTH 97 5.5 SOLVENT
COMPOSITION 97 6. CONCLUSIONS 98 REFERENCES 99 CHAPTER 5 GENETICS OF
SIDEROPHORE BIOSYNTHESIS AND TRANSPORT VOLKMAR BRAUN 1. STRUCTURE AND
FUNCTION OF SIDEROPHORES 103 2. F 3+ -AEROBACTIN TRANSPORT SYSTEM 104
CONTENTS . IX 2.1 BIOSYNTHESIS OF AEROBACTIN 104 2.2 FE 3+ -AEROBACTIN
TRANSPORT ILL 3. ENTEROCHELIN BIOSYNTHESIS AND FE 3+ -ENTEROCHELIN
TRANSPORT 113 4. FE 3+ -DICITRATE TRANSPORT 115 4.1 TRANSPORT 115 4.2
REGULATION 117 5. REGULATION OF IRON TRANSPORT SYSTEMS 118 5.1
REGULATION OF GENE EXPRESSION 118 5.2 REGULATION OF THE FE 3+
-SIDEROPHORE RECEPTOR ACTIVITY 120 6. ANTIBIOTICS CONTAINING SIDEROPHORE
STRUCTURES 122 6.1 NATURALLY OCCURRING SIDEROMYCINS 122 6.2 SYNTHETIC
ANTIBIOTICS WITH SIDEROPHORE STRUCTURES 123 7. CONCLUDING REMARKS 124
ACKNOWLEDGEMENTS 125 REFERENCES 125 CHAPTER 6 DISCOVERY OF NEW /?-LACTAM
AND /?-LACTAM LIKE ANTIBIOTICS FROM BACTERIA HIDEO ONO AND SETSUO HARADA
1. INTRODUCTION . 131 2. SCREENING METHOD AND PRODUCING ORGANISMS 134 3.
FERMENTATION 135 4. ISOLATION PROCEDURE 135 5. CHEMICAL CHARACTERIZATION
140 6. STRUCTURE DETERMINATION 142 7. BIOLOGICAL ACTIVITIES OF
CEPHABACIN, FORMADICIN AND LACTIVICIN 147 8. CONCLUSION . 155 REFERENCES
. 155 CHAPTER 7 GLYCOPEPTIDE ANTIBIOTICS OF THE VANCOMYCIN GROUP C.
LANCINI AND B. CAVALLERI 1. INTRODUCTION 159 2. PRODUCING ORGANISMS 161
3. CHEMISTRY 161 4. BIOSYNTHESIS 167 5. MECHANISM OF ACTION 169 5.1
EFFECT ON GROWING CULTURES 169 5.2 STUDIES WITH CELL FREE SYSTEMS 169
5.3 ACTION AT MOLECULAR LEVEL 170 6. RELATION OF ANTIMICROBIAL ACTIVITY
AND MECHANISM OF ACTION 171 REFERENCES 172 X CONTENTS CHAPTER 8 PEPTIDE
PHYTOTOXINS FROM PLANT PATHOGENIC FUNGI JONATHAN D. WALTON 1.
INTRODUCTION 179 2. HOST-SELECTIVE TOXINS 181 2.1 AM-TOXIN 181 2.2
HOST-SPECIFIC TOXIN FROM ALTERNARIA BRASSICAE 183 2.3 VICTORIN 184 2.4
HC-TOXIN 188 2.5 PC-TOXIN 192 3. NON-SELECTIVE TOXINS 193 3.1 TENTOXIN
194 3.2 ENNIATINS 196 3.3 PEPTIDIC SIDEROPHORES 196 REFERENCES 198
CHAPTER 9 CHEMICAL SYNTHESIS AND BIOACTIVITY OF GRAMICIDIN S AND RELATED
PEPTIDES MICHINORI WAKI AND NOBUO IZUMIYA 1. INTRODUCTION 205 2.
STRUCTURES OF GRAMICIDIN S AND RELATED NATURAL PEPTIDES 206 2.1
GRAMICIDIN S AND ITS CONGENERS 206 2.2 TYROCIDINES 207 2.3 GRATISIN 208
3. CHEMICAL SYNTHESIS OF GRAMICIDIN S AND RELATED PEPTIDES 208 3.1
SYNTHESIS OF LINEAR PRECURSOR PEPTIDES 208 3.2 SYNTHESIS OF CYCLIC
PEPTIDES 209 4. STRUCTURE-ACTIVITY RELATIONSHIPS OF GRAMICIDIN S,
TYROCIDINES AND GRATISIN 212 4.1 GRAMICIDIN S 212 4.1.1 FUNKTION OF THE
AMINO ACID RESIDUES AT POSITIONS 1 AND 1 . . . 216 4.1.2 FUNKTION OF
THE AMINO ACID RESIDUES AT POSITIONS 2 AND 2 . . . 217 4.1.3 FUNCTION
OF THE AMINO ACID RESIDUES AT POSITIONS 1,1 AND 3,3 * 217 4.1.4
FUNCTION OF THE AMINO ACID RESIDUES AT POSITIONS 3 AND 3 . . . 217
4.1.5 FUNCTION OF THE AMINO ACID RESIDUES AT POSITIONS 4 AND 4 . . .
218 4.1.6 FUNCTION OF THE AMINO ACID RESIDUES AT POSITIONS 5 AND 5 . .
. 218 4.1.7 SUMMARY BY SIDEDNESS HYPOTHESIS 218 4.2 TYROCIDINES 219
4.3 GRATISIN 221 5. CONFORMATIONS OF GRAMICIDIN S AND TYROCIDINES 221
5.1 OPTICAL ROTATORY DISPERSION (ORD) AND CIRCULAR DICHROISM (CD) . . .
222 5.2 NUCLEAR MAGNETIC RESONANCE (NMR) 223 5.3 OTHER CONFORMATIONAL
ANALYSES 224 6. DESIGN OF HIGHLY ACTIVE ANALOGS OF GRAMICIDIN S 224
CONTENTS XI 7. ACTIVE ANALOGS OF GRAMICIDIN S AGAINST GRAM-NEGATIVE
BACTERIA 228 8. MECHANISM OF ANTIMICROBIAL ACTION OF GRAMICIDIN S 230
8.1 INTERACTIONS WITH MODEL MEMBRANES 230 8.2 INTERACTIONS WITH
BACTERIAL MEMBRANES 230 9. CONCLUDING REMARKS 234 REFERENCES 234 CHAPTER
10 CYCLOSPORINE: SYNTHETIC STUDIES, STRUCTURE-ACTIVITY RELATIONSHIPS,
BIOSYNTHESIS AND MODE OF ACTION HANS G. FLIRI AND ROLAND M. WEGNER 1.
INTRODUCTION 246 2. CYCLOSPORINE 250 2.1 ISOLATION 250 2.2 STRUCTURE
DETERMINATION 250 2.3 OTHER NATURALLY OCCURRING CYCLOSPORINES.
NOMENCLATURE 252 3. TOTAL SYNTHESIS . 253 3.1 SYNTHESIS OF MEBMT 254
3.1.1 THE WENGER SYNTHESIS 254 3.1.2 THE EVANS SYNTHESIS 256 3.1.3 THE
SEEBACH SYNTHESIS 258 3.1.4 THE SYNTHESES OF RICH 258 3.1.5 THE SCHMIDT
SYNTHESIS 259 3.2 SYNTHESIS OF CYCLOSPORINE 262 4. CHEMICAL MODIFICATION
OF CYCLOSPORINE 266 5. STRUCTURE-ACTIVITY RELATIONSHIPS 267 6.
CONFORMATION OF CYCLOSPORINE IN THE CRYSTAL, IN APROTIC SOLVENTS AND IN
BIOLOGICAL FLUIDS .270 6.1 CRYSTAL AND SOLUTION CONFORMATION 270 6.2
CYCLOSPORINE CONFORMATION IN BIOLOGICAL FLUIDS 271 6.3 IMMUNOCHEMICAL
STUDY OF THE CYCLOSPORINE CONFORMATION IN AQUEOUS MEDIUM 271 6.4
IMMUNOLOGICAL STUDIES OF CYCLOSPORINE AND THEIR INTERPRETATION IN TERMS
OF THE CONFORMATION OF THE COMPOUND IN AQUEOUS MEDIA 271 6.5
CALCULATIONS USING MOLECULAR DYNAMICS PROGRAMS INDICATE THAT THE CRYSTAL
STRUCTURE CONFORMATION IS IN WATER MORE STABLE THAN ANY OTHERS 273 7.
BIOSYNTHESIS 274 8. MECHANISM OF ACTION OF CYCLOSPORINE 276 8.1 EFFECTS
ON T CELLS 277 8.2 EFFECTS ON B CELLS 279 8.3 POSSIBLE INTRACELLULAR
TARGETS FOR CYCLOSPORINE 280 9. CONCLUSIONS AND OUTLOOK 280 REFERENCES
282 XII CONTENTS CHAPTER 11 BIOSYNTHESIS AND CHEMICAL SYNTHESIS OF
BLEOMYCIN TOMOHISA TAKITA AND YASUHIKO MURAOKA 1. INTRODUCTION 289 2.
BIOSYNTHESIS AND SEMISYNTHESIS OF UNNATURAL CONGENERS 292 2.1
BIOSYNTHESIS 292 2.2 SEMISYNTHESIS 294 3. BIOSYNTHESIS AND CHEMICAL
SYNTHESIS OF BUILDING BLOCKS OF BLEOMYCIN MOLECULE 295 3.1 BIOSYNTHESIS
OF UNUSUAL AMINO ACIDS 295 3.2 CHEMICAL SYNTHESIS OF UNUSUAL AMINO ACIDS
297 3.2.1 SYNTHESIS OF PYRIMIDINE-CONTAINING AMINO ACID (PBA) 297 3.2.2
SYNTHESIS OF ERJ//ZRO-/?-HYDROXY-L-HISTIDINE 298 3.2.3 SYNTHESIS OF
(2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYLPENTANOIC ACID (AHM) 299 3.2.4
SYNTHESIS OF 2 -(2-AMINOETHYL)-2,4 -BITHIAZOLE-4-CARBOXYLIC ACID (ABC)
300 4. BIOSYNTHETIC AND CHEMICAL CONSTRUCTION OF BLEOMYCIN MOLECULE 300
4.1 BIOSYNTHESIS OF PEPTIDE PART OF BLEOMYCIN: DEGLYCOBLEOMYCIN 300 4.2
CHEMICAL SYNTHESIS OF DEGLYCOBLEOMYCIN 302 4.3 CHEMICAL SYNTHESIS OF THE
DISACCHARIDE MOIETY FOR TOTAL SYNTHESIS OF BLEOMYCIN 303 4.4 TOTAL
SYNTHESIS OF BLEOMYCIN 304 5. CONCLUSION 306 REFERENCES 307 CHAPTER 12
SMALL MOLECULAR PROTEASE INHIBITORS AND THEIR BIOLOGICAL EFFECTS TAKAAKI
AOYAGI 1. INTRODUCTION 311 2. PROTEASE INHIBITORS 312 3. INHIBITORS
AGAINST ENDOPEPTIDASES ..313 4. ENZYMATIC ACTIVITIES OF CELLULAR
MEMBRANE 317 5. INHIBITORS AGAINST CELL SURFACE ENZYMES 320 5.1
INHIBITORS AGAINST EXOPEPTIDASES 320 5.2 INHIBITORS AGAINST ENZYMES ON
CELLULAR MEMBRANE 328 6. ENZYMATIC CHANGES IN VARIOUS PATHOLOGIC
CONDITIONS 330 6.1 ROLES OF CATABOLIC ENZYMES IN MUSCULAR DYSTROPHY 330
6.1.1 MURINE MUSCULAR DYSTROPHY 330 6.1.2 DUCHENNE MUSCULAR DYSTROPHY
335 6.2 SPONTANEOUSLY HYPERTENSIVE RATS AND AMINOPEPTIDASES 337 6.3
IMMUNOLOGIC DISEASES AND HYDROLYTIC ENZYMES 342 CONTENTS XIII 7.
MODIFICATION OF METABOLIC HOMEOSTASIS CAUSED BY LOW-MOLECULAR-WEIGHT
ENZYME INHIBITORS 346 7.1 ENZYMATIC OSCILLATIONS CAUSED BY BESTATIN 346
7.2 INFLUENCE OF ANGIOTENSIN-CONVERTING ENZYME INHIBITOR, FOROXYMITHINE
349 7.3 EFFECTS OF BESTATIN ON HYDROLYTIC ENZYMES IN PROGRESSIVE
MUSCULAR DYSTROPHY 352 8. PHARMACOLOGIC APPLICATIONS OF ENZYME
INHIBITORS 356 9. SUMMARY 358 ACKNOWLEDGEMENTS 359 REFERENCES 359
CHAPTER 13 DIRECTED BIOSYNTHESIS OF NEOVIRIDOGRISEINS YASUSHI OKUMURA 1.
INTRODUCTION 365 2. SELECTIVE PRODUCTION OF NEOVIRIDOGRISEINS BY
DIRECTED BIOSYNTHESIS . . . . 367 2.1 EFFECT OF EXOGENOUS AMINO ACID ON
THE PRODUCTION OF NEOVIRIDOGRISEINS 368 2.2 SPECIFIC ACCUMULATION OF
NEOVIRIDOGRISEIN II BY INHIBITION OF PROLINE HYDROXYLATION REACTION 371
2.3 SPECIFIC ACCUMULATION OF NEOVIRIDOGRISEIN II BY THE MUTANT BLOCKED
IN ZRAN.Y-4-HYDROXY-L-PROLINE FORMATION FROM L-PROLINE 374 3. SUMMARY
377 REFERENCES 377 CHAPTER 14 BIOCHEMICAL GENETICAL AND BIOTECHNICAL
ASPECTS OF ANTIBIOTIC PRODUCTION VIA IMMOBILISED BIOCATALYSIS ERICK J.
VANDAMME 1. NOVEL ANTIBIOTIC COMPOUNDS 379 2. NOVEL PRODUCTION WAYS FOR
ANTIBIOTICS 381 3. TOTAL ENZYMATIC SYNTHESIS OF ANTIBIOTICS 381 4.
PARTIAL ENZYMATIC SYNTHESIS OF ANTIBIOTICS 386 5. ANTIBIOTIC
FERMENTATION VIA IMMOBILISED VIABLE CELLS 390 6. JS-LACTAM-ANTIBIOTIC
BIOCONVERSIONS WITH IMMOBILISED BIOCATALYSTS . . . 392 6.1 PENICILLIN
BIOCONVERSIONS 392 6.2 CEPHALOSPORIN BIOCONVERSIONS 397 7. CHIRAL
SIDE-CHAIN PRODUCTION FOR /?-LACTAM ANTIBIOTICS SYNTHESIS . . . . 402 8.
BIOCONVERSION OF NOVEL /?-LACTAM ANTIBIOTICS 403 9. BIOCONVERSION OF
OTHER IMPORTANT ANTIBIOTICS 404 10. PERSPECTIVES 406 REFERENCES 407 XIV
CONTENTS CHAPTER 15 COMPILATION OF PEPTIDE STRUCTURES * A BIOGENETIC
APPROACH HANS VON DOHREN INTRODUCTION 411 GENERAL BIOSYNTHETIC MECHANISM
411 COMPOUND DATA 412 ABBREVIATIONS AND SYMBOLISM 412 CONFIGURATION 412
BONDS 412 ABBREVIATED NOMENCLATURE USED 412 CYCLIC STRUCTURES 413 SIDE
CHAIN MODIFICATIONS 413 CHAIN LENGTH 413 COMBINATIONS OF CHAINS 413
PIPERIDINE-TYPE CYCLIZATIONS 414 UNUSUAL CONSTITUENTS 414 COMPILATION
415 INDEX OF TABLE 495 LIST OF ABBREVIATIONS 502 A) COMPOUNDS 502 B)
SOURCES 507 LIST OF CONTRIBUTORS 509 INDEX 511
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| spelling | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides ed. Horst Kleinkauf ; Hans von Döhren Berlin ; New York <<de>> Gruyter 1990 XIV, 522 S. Ill. txt rdacontent n rdamedia nc rdacarrier Biochemie (DE-588)4006777-4 gnd rswk-swf Peptidantibiotikum (DE-588)4173714-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Peptidantibiotikum (DE-588)4173714-3 s Biochemie (DE-588)4006777-4 s DE-604 Kleinkauf, Horst 1930-2020 Sonstige (DE-588)105576891 oth GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=001617682&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides Biochemie (DE-588)4006777-4 gnd Peptidantibiotikum (DE-588)4173714-3 gnd |
| subject_GND | (DE-588)4006777-4 (DE-588)4173714-3 (DE-588)4143413-4 |
| title | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides |
| title_auth | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides |
| title_exact_search | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides |
| title_full | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides ed. Horst Kleinkauf ; Hans von Döhren |
| title_fullStr | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides ed. Horst Kleinkauf ; Hans von Döhren |
| title_full_unstemmed | Biochemistry of peptide antibiotics recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides ed. Horst Kleinkauf ; Hans von Döhren |
| title_short | Biochemistry of peptide antibiotics |
| title_sort | biochemistry of peptide antibiotics recent advances in the biotechnology of beta lactams and microbial bioactive peptides |
| title_sub | recent advances in the biotechnology of Beta-lactams and microbial bioactive peptides |
| topic | Biochemie (DE-588)4006777-4 gnd Peptidantibiotikum (DE-588)4173714-3 gnd |
| topic_facet | Biochemie Peptidantibiotikum Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=001617682&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT kleinkaufhorst biochemistryofpeptideantibioticsrecentadvancesinthebiotechnologyofbetalactamsandmicrobialbioactivepeptides |