The practice of peptide synthesis:
Gespeichert in:
| Hauptverfasser: | , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Berlin u.a.
Springer
1994
|
| Ausgabe: | 2., rev. ed. |
| Schriftenreihe: | Springer lab manual
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVIII, 217 S. graph. Darst. |
| ISBN: | 3540575057 0387575057 |
Internformat
MARC
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| 084 | |a VK 8560 |0 (DE-625)147540:253 |2 rvk | ||
| 084 | |a CHE 820f |2 stub | ||
| 100 | 1 | |a Bodanszky, Miklos |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a The practice of peptide synthesis |c M. Bodanszky ; A. Bodanszky |
| 250 | |a 2., rev. ed. | ||
| 264 | 1 | |a Berlin u.a. |b Springer |c 1994 | |
| 300 | |a XVIII, 217 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Springer lab manual | |
| 650 | 4 | |a Peptides - Synthèse | |
| 650 | 7 | |a Produtos naturais (quimica organica) |2 larpcal | |
| 650 | 4 | |a Peptides |x Synthesis | |
| 650 | 0 | 7 | |a Methode |0 (DE-588)4038971-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Peptidsynthese |0 (DE-588)4173715-5 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Peptidsynthese |0 (DE-588)4173715-5 |D s |
| 689 | 0 | 1 | |a Methode |0 (DE-588)4038971-6 |D s |
| 689 | 0 | |8 1\p |5 DE-604 | |
| 700 | 1 | |a Bodanszky, Agnes |e Verfasser |4 aut | |
| 856 | 4 | 2 | |m SWB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006289078&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-006289078 | ||
| 883 | 1 | |8 1\p |a cgwrk |d 20201028 |q DE-101 |u https://d-nb.info/provenance/plan#cgwrk | |
Datensatz im Suchindex
| _version_ | 1804123861347729408 |
|---|---|
| adam_text | IMAGE 1
CONTENTS
I INTRODUCTION 1
II PROTECTING GROUPS 7
1 INTRODUCTION OF AMINE PROTECTING GROUPS 9
1.1 THE P-TOLUENESULFONYL GROUP 9
P-TOLUENESULFONYL-L-ISOLEUCINE 9
1.2 PHTHALYL (PHTHALOYL, PHT) AMINO ACIDS 10
PHTHALYL-L-LEUCINE 10
1.3 THE BENZYLOXYCARBONYL GROUP 11
BENZYLOXYCARBONYL-L-PROLINE 11
BENZYLOXYCARBONYL-L-LEUCINE 11
JV A -BENZYLOXYCARBONYL-L-ARGININE 12
BENZYLOXYCARBONYL-L-ASPARTIC ACID SS-BENZYL ESTER . .. 12 1.4
4-METHOXYBENZYLOXYCARBONYLAMINO ACIDS 14
1.5 THE TERT-BUTYLOXYCARBONYL (BOC) GROUP 15
1.5.1 INTRODUCTION OF THE TERT-BUTYLOXYCARBONYL GROUP WITH
2-TERT-BUTYLOXYCARBONYLOXIMINO-2- PHENYLACETONITRILE 15
TER F-BUTYLOXYCARBONYL-GLYCINE 16
TERT-BUTYLOXYCARBONYL-L-TRYPTOPHAN 16
1.5.2 INTRODUCTION OF THE FERF-BUTYLOXYCARBONYL GROUP WITH TERT-BUTYL
PYROCARBONATE 17
1.6 THE BIPHENYLYLISOPROPYLOXYCARBONYL (BPOC) GROUP . . 18
BPOC-L-LEUCINE 18
BPOC-L-LEUCINE 19
1.7 THE 9-FLUORENYLMETHYLOXYCARBONYL (FMOC) GROUP . .. 20
9-FLUORENYLMETHYL CHLOROCARBONATE 20
9-FLUORENYLMETHYLOXYCARBONYL-L-TRYPTOPHAN 21
1.8 O-NITROPHENYLSULFENYLAMINO ACIDS 21
1.9 2-TRIMETHYLSILYLETHYLOXYCARBONYLAMINO ACIDS 22
4-NITROPHENYL-2-TRIMETHYLSILYLETHYL CARBONATE 22
2-TRIMETHYLSILYLETHYLOXYCARBONYL-L-PROLINE 23
1.10 MALEOYLAMINO ACIDS AND MALEOYL-PEPTIDES 24
N-METHOXYCARBONYLMALEIMIDE 24
IMAGE 2
X CONTENTS
MALEOYL-GLYCINE 24
MALEOYL PEPTIDES 25
1.11 T R I P H E N Y L M E T H Y L - A M I NO ACIDS 26
TRITYL-L-LEUCINE 26
IV-TRITYL A M I NO ACIDS 27
2 BLOCKING OF THE A-CARBOXYL G R O UP 28
2.1 METHYL ESTERS 28
2.2 ETHYL ESTERS 29
2.2.1 ESTERIFICATION WITH THE H E LP OF G A S E O US HC1 . .. 29
L-TYROSINE ETHYL ESTER 29
2.2.2 ESTERIFICATION CATALYZED BY P-TOLUENESULFONIC ACID 30 L-METHIONINE
ETHYL ESTER P-TOLUENESULFONATE . .. 30
2.3 BENZYL ESTERS 30
GLYCINE BENZYL ESTER P-TOLUENESULFONATE 30
TERT-BUTYLOXYCARBONYL-L-ASPARAGINE BENZYL ESTER . . .. 31
L-GLUTAMIC ACID A-BENZYL ESTER 32
2.3.1 POLYMERIC BENZYL ESTERS 33
H Y D R O X Y M E T H Y L - P O L Y M ER 33
TERT-BUTYLOXYCARBONYL-GLYCYL RESIN 33
BENZYLOXYCARBONYL-L-ISOLEUCYL-POLYMER 34
2.4 4-NITROBENZYL ESTERS 34
L-ALANINE-4-NITROBENZYL ESTER P-TOLUENESULFONATE . .. 34
2.5 4-METHOXYBENZYL ESTERS OF IV*-PROTECTED AMINO ACIDS . .. 35
BENZYLOXYCARBONYLGLYCINE 4-METHOXYBENZYL ESTER . .. 35
2.6 BENZHYDRYL ESTERS (DIPHENYLMETHYL ESTERS) 36
2.7 P H T H A L I M I D O M E T H YL ESTERS 37
2.8 TERT-BUTYL ESTERS 38
ADDITION OF IV A -ACYLAMINO ACIDS TO ISOBUTYLENE . . .. 38 L-PROLINE
TERT-BUTYL ESTER 38
TRANSESTERIFICATION WITH TERT-BUTYL ACETATE 39
ESTERIFICATION OF FREE AMINO ACIDS THROUGH ACID CATALYZED ADDITION TO
ISOBUTYLENE 39
L-TYROSINE TERT-BUTYL ESTER 39
2.9 PHENACYL ESTERS 40
BENZYLOXYCARBONYLGLYCINE PHENACYL ESTER 40
2.10 2-TRIMETHYLSILYLETHYL ESTERS 41
2.11 4-PICOLYL ESTERS 41
BENZYLOXYCARBONYL-L-PHENYLALANINE 4-PICOLYL ESTER. . . 41
BENZYLOXYCARBONYL-L-VALINE 4-PICOLYL ESTER 42
2.12 9-FLUORENYLMETHYL ESTERS 43
TERT-BUTYLOXYCARBONYL-L-PHENYLALANINE 9-FLUORENYLMETHYL ESTER 43
2.13 2-BENZYLOXYPHENYL ESTERS 44
L-ALANINE 2-BENZYLOXYPHENYL ESTER HYDROCHLORIDE . .. 44
IMAGE 3
CONTENTS XT
2.14 PHENYL ESTERS 45
2.15 ALLYL ESTERS 45
PROTECTION OF SIDE CHAIN FUNCTIONS 47
3.1 SERINE ETHERS 47
IV-TERI-BUTYLOXYCARBONYL-O-BENZYL-L-SERINE CYCLOHEXYLAMMONIUM SAIT 47
3.2 ETHERS OF THREONINE 48
O-FERT-BUTYL-L-THREONINE 48
3.3 TYROSINE ETHERS 50
O-BENZYL-L-TYROSINE 50
3.4 ACYLATION OF THE E-AMINO GROUP OF LYSINE 51
JV E -TRIFLUOROACETYL-LYSINE 51
N -P-TOLUENESULFONYL-L-LYSINE 52
3.5 PROTECTION OF THE GUANIDINO GROUP OF ARGININE . . .. 53
NITRO-L-ARGININE 53
JV A -BENZYLOXYCARBONYL-JV G -P-TOLUENESULFONYL-L-ARGININE 54 JV A
-BENZYLOXYCARBONYL-IV I , AT-BIS- (L-ADAMANTYLOXYCARBONYL)-L-ARGININE
56
N A - 4 -METHOXYBENZYLOXYCARBONYL- IV G -MESITYLENE- SULFONYL-L-ARGININE
CYCLOHEXYLAMMONIUM SAIT 57 JV G
-4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL-L- ARGININE 57
3.6 MASKING THE IMIDAZOLE IN HISTIDINE 59
3.6.1 IV IM -P-TOLUENESULFONYL-L-HISTIDINE 59
JV*-BENZYLOXYCARBONYL-IV IM -TOSYL-L-HISTIDINE . .. 59 3.6.2 N A
-FERF-BUTYLOXYCARBONYL-IV I -BENZYLOXYRNETHYL-L- HISTIDINE 60
3.6.3 IV IM -TRITYL-L-HISTIDINE 62
3.7 BLOCKING OF THE INDOLE NITROGEN IN TRYPTOPHAN 62
N IM - FORMYL-L-TRYPTOPHAN 62
3.8 PROTECTION OF SIDE CHAIN CARBOXYL GROUPS 63
L-ASPARTIC ACID SS-BENZYL ESTER (/?-BENZYL-L-ASPARTATE) . 63 L-GLUTAMIC
ACID Y-TERT-BUTY ESTER 64
3.9 PROTECTION OF THE CARBOXAMIDE FUNCTION 65
INTRODUCTION OF THE 4,4 -DIMETHOXYBENZHYDRYL GROUP . 65 3.10 BLOCKING
THE SULFHYDRYL GROUP IN CYSTEINE 66
S-BENZYL-L-CYSTEINE 66
S-ETHYLCARBAMOYL-L-CYSTEINE 67
S-ACETAMIDOMETHYL-L-CYSTEINE 68
S-TRIPHENYLMETHYL-L-CYSTEINE (S-TRITYL-L-CYSTEINE). . .. 68
JV-TERF-BUTYLOXYCARBONYL-S-(3-NITRO-2-PYRIDINESULFENYL- L-CYSTEINE 69
S-FERF-BUTYL-L-CYSTEINE HYDROCHLORIDE 71
3.11 PROTECTION OF THE THIOETHER IN METHIONINE 72
IMAGE 4
XII CONTENTS
L-METHIONINE SULFOXIDE 72
N-TERT-BUTYLOXYCARBONYL-S-METHYL-L-METHIONINE P-NITROPHENYL ESTER
P-TOLUENESULFONATE 72
III ACTIVATION AND COUPLING 75
1 THE ACID CHLORIDE PROCEDURE 77
P-TOLUENESULFONYL-L-ISOLEUCYL-GLYCINE ETHYL ESTER 77
P-TOLUENESULFONYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINE... 77 2 THE
AZIDE PROCESS 79
2.1 PEPTIDE HYDRAZIDES THROUGH HYDRAZINOLYSIS OF PEPTIDE ESTERS 79
JV-BENZYLOXYCARBONYL-S-BENZYL-L-CYSTEINYL-L-SERYL-L- HISTIDINE HYDRAZIDE
79
2.2 PREPARATION OF PEPTIDE HYDRAZIDES FROM CARBOXYLIC ACIDS 80
TERF-BUTYLOXYCARBONYL-SS-BENZYL-L-ASPARTYL-L-LEUCYL-L-
W-BENZYLOXYCARBONYL-LYSINE HYDRAZIDE 80
2.3 PROTECTED HYDRAZIDES 81
JV-BENZYLOXYCARBONYL-L-PROLYL-GLYCYL-IV -F ?RT
BUTYLOXYCARBONYL-HYDRAZINE 81
N-BENZYLOXYCARBONYL-GLYCYL-GLYCYL-IV -IERI-BUTYLOXY- CARBONYL-HYDRAZINE
81
GLYCINE BENZYLOXYCARBONYLHYDRAZIDE TRIFLUOROACETATE. 82 2.4 CONVERSION
OF HYDRAZIDES TO AZIDES AND COUPLING WITH AZIDES 83
2.4.1 GENERATION OF THE AZIDE WITH THE AID OF SODIUM NITRITE AND
COUPLING 83
BENZYLOXYCARBONYL-L-SERYL-L-TYROSYL-L-SERYL-L-
METHIONYL-Y-BENZYL-L-GLUTAMIC ACID 83
2.4.2 CONVERSION OF A HYDRAZIDE TO THE AZIDE WITH THE AID OF BUTYL
NITRITE AND ACYLATION WITH THE AZIDE IN SITU 84
BENZYLOXYCARBONYL-L-TYROSYL-L-ISOLEUCYL-L-
GLUTAMINYL-L-ASPARAGINYL-S-BENZYL-L-CYSTEINYL-L-
PROLYL-L-LEUCYL-GLYCINAMIDE 84
2.4.3 CONVERSION OF PROTECTED AMINO ACID OR PEPTIDE HYDRAZIDES TO THE
AZIDES FOLLOWED BY ACYLATION WITH THE ISOLATED AZIDE 85
3 SYMMETRICAL ANHYDRIDES 87
FERF-BUTYLOXYCARBONYL-L-PHENYLALANINE ANHYDRIDE 87 4 MIXED ANHYDRIDES 89
IMAGE 5
CONTENTS XIII
4.1 THE ISOVALERIC ACID MIXED ANHYDRIDE METHOD 89
BENZYLOXYCARBONYL-L-LEUCYL-GLYCINE ETHYL ESTER 89 4.2 TRIMETHYLACETIC
ACID (PIVALIC ACID) MIXED ANHYDRIDES. 90
BENZYLOXYCARBONYL-A-METHYLALANYL-A-METHYLALANINE METHYL ESTER 90
JV^-BENZYLOXYCARBONYL-./V -P-TOLUENESULFONYL-L- LYSYLGLYCINE ETHYL ESTER
91
4.3 THE ETHYL CARBONATE MIXED ANHYDRIDE METHOD . . .. 92
BENZYLOXYCARBONYL-L-LEUCYL-GLYCINE ETHYL ESTER 92 4.4 ISOBUTYLCARBONIC
ACID MIXED ANHYDRIDES 93
BENZYLOXYCARBONYL-GLYCYL-L-PHENYLALANYL-GLYCINE ETHYL ESTER 93
4.5 COUPLING WITH THE AID OF O-PHENYLENE PHOSPHOROCHLORIDITE 94
PREPARATION OF JV-BENZYLOXYCARBONYL-S-BENZYL-L-CYSTEINYL-
L-TYROSYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINYL-S-BENZYL-
L-CYSTEINYL-L-PROLYL-L-LEUCYL-GLYCINE AMIDE 94
PREPARATION OF ACTIVE ESTERS 96
5.1 CYANOMETHYL ESTERS 96
JV-BENZYLOXYCARBONYL-S-BENZYL-L-CYSTEINE CYANOMETHYL ESTER 96 5.2
PREPARATION OF P-NITROPHENYL ESTERS 97
BENZYLOXYCARBONYL-L-PHENYLALANINE P-NITROPHENYL ESTER 97 5.3
O-NITROPHENYL ESTERS 98
TERF-BUTYLOXYCARBONYL-GLYCINE O-NITROPHENYL ESTER . .. 98 5.4
2,4-DINITROPHENYL ESTERS . 99
YV-BENZYLOXYCARBONYL-L-THREONINE 2,4-DINITROPHENYL ESTER 99
5.5 2,4,5-TRICHLOROPHENYL ESTERS 100
5.6 PENTACHLOROPHENYL ESTERS 101
BENZYLOXYCARBONYL-GLYCYL-L-PHENYLALANINE PENTACHLOROPHENYL ESTERS 101
5.7 PENTAFLUOROPHENYL ESTERS 102
BENZYLOXYCARBONYL-GLYCYL-L-PHENYLALANINE PENTAFLUOROPHENYL ESTER 102
TERT-BUTYLOXYCARBONYLAMINO ACID PENTAFLUOROPHENYL ESTERS 103
5.8 IV-HYDROXYPHTHALIMIDE ESTERS 103
5.9 JV-HYDROXYSUCCINIMIDE ESTERS 104
TERT-BUTYLOXYCARBONYL-L-ALANINE IV-HYDROXYSUCCINIMIDE ESTER 104
5.10 1-HYDROXYPIPERIDINE ESTERS 105
BENZYLOXYCARBONYL-L-LEUCINE 1-HYDROXYPIPERIDINE ESTER 105 5.11 ESTERS OF
5-CHLORO-8-HYDROXY-QUINOLINE 106
IMAGE 6
XIV CONTENTS
6 COUPLING WITH ACTIVE ESTERS 108
6.1 COUPLING IN ORGANIC SOLVENTS 108
6.1.1 ACYLATION WITH CYANOMETHYL ESTERS 108
IV-BENZYLOXYCARBONYL-S-BENZYL-L-CYSTEINYL-L- TYROSINE 108
6.1.2 CHAIN LENGTHENING WITH P-NITROPHENYL ESTERS. . . 109
BENZYLOXYCARBONYL-L-ASPARAGINYL-S-BENZYL-L-
CYSTEINYL-L-PROLYL-L-LEUCYL-GLYCINAMIDE 109 6.1.3 ACYLATION WITH
AF-HYDROXYSUCCINIMIDE ESTERS . .. 110
FERT-BUTYLOXYCARBONYL-GLYCYL-L-PHENYLALANYL- GLYCINE ETHYL ESTER 110
BENZYLOXYCARBONYL-L-PHENYLALANYL-L-TYROSINE ETHYL ESTER I LL
6.1.4 COUPLING WITH 2,4-DINITROPHENYL ESTERS 112
BENZYLOXYCARBONYL-L-THREONYL-L-ALANYL-L-ALANYL- L-ALANINE ETHYL ESTER
112
6.2 COUPLING IN ORGANIC-AQUEOUS MEDIA 113
6.2.1 ACYLATION WITH P-NITROPHENYL ESTERS 113
BENZYLOXYCARBONYL-L-PHENYLALANYL-GLYCYL-L- PROLINE 113
6.2.2 ACYLATION WITH JV-HYDROXYSUCCINIMIDE ESTERS . .. 114
BENZYLOXYCARBONYL-GLYCYL-L-PROLINE 114
BENZYLOXYCARBONYL-L-PROLYL-GLYCINE 114
6.3 CATALYSIS OF ACTIVE ESTER REACTIONS 115
6.3.1 CATALYSIS WITH IMIDAZOLE 115
BENZYLOXYCARBONYL-L-PROLYL-L-TYROSINE METHYL ESTER 115
6.3.2 CATALYSIS WITH 1-HYDROXYBENZOTRIAZOLE 116
BENZYLOXYCARBONYL-L-LEUCYL-L-VALINAMIDE 116 6.3.3 CATALYSIS WITH
3-HYDROXY-3,4-DIHYDRO-QUINAZOLINE- 4-ONE 116
BENZYLOXYCARBONYL-L-ISOLEUCYL-GLYCINAMIDE . . .. 116 7 PEPTIDE BOND
FORMATION WITH THE AID OF COUPLING REAGENTS 118 7.1 THE
DICYCLOHEXYLCARBODIIMIDE (DCC, DCCI) METHOD . 118 7.1.1 COUPLING WITH
DCC 118
IV-PHTHALOYL-L-THREONYL-L-PHENYLALANINE METHYL ESTER 118
7.1.2 COUPLING WITH CARBODIIMIDES IN THE PRESENCE OF
1-HYDROXYBENZOTRIAZOLE 119
TERT-BUTYLOXYCARBONYL-L-LEUCYL-L-PHENYLALANINE METHYL ESTER 119
7.1.3 COUPLING WITH DICYCLOHEXYLCARBODIIMIDE IN THE PRESENCE OF
IV-HYDROXYSUCCINIMIDE 120
PHTHALYL-L-PHENYLALANYL-L-VALYL-L-GLUTAMINYL-L-
IMAGE 7
CONTENTS XV
TRYPTOPHYL-L-LEUCYL-L-METHIONYL-L-ASPARAGINYL- O-TERF-BUTYL-L-THREONINE
TERI-BUTYL ESTER 120
N-BENZYLOXYCARBONYL-0-TERT-BUTYL-L-TYROSYL-L-
LEUCYL-/?-TETT-BUTYL-L-ASPARTIC ACID METHYL ESTER. 121 7.2 COUPLING WITH
L-ISOBUTYLOXYCARBONYL-2-ISOBUTYLOXY- 1,2-DIHYDROQUINOLINE (IIDQ) 121
BENZYLOXYCARBONYL-L-ALANYL-L-TYROSINE METHYL ESTER . . 121 7.3 THE
CARBONYLDIIMIDAZOLE METHOD 122
BENZYLOXYCARBONYL-GLYCYL-L-TYROSINE ETHYL ESTER . . .. 122 7.4 COUPLING
WITH IV-ETHYL-5-PHENYLISOXAZOLIUM-3 - SULFONATE 123
N , IV E -DIBENZYLOXYCARBONYL-L-LYSYL-GLYCINE ETHYL ESTER 123 7.5
COUPLING WITH 1-BENZOTRIAZOLYL-TRI-DIMETHYLAMINO- PHOSPHONIUM
HEXAFLUOROPHOSPHATE (BOP-REAGENT) . . 124 7.6
O-BENZOTRIAZOLYL-TETRAMETHYLURONIUM
HEXAFLUOROPHOSPHATE 125
PREPARATION OF THE HBTU-REAGENT 125
COUPLING WITH HBTU 125
IV REMOVAL OF PROTECTING GROUPS 127
1 HYDROGENATION 129
1.1 HYDROGENOLYSIS OF BENZYL ESTERS, BENZYL ETHERS AND OF THE
BENZYLOXYCARBONYL GROUP 129
L-PROLYL-L-LEUCYL-GLYCINAMIDE 129
1.2 CATALYTIC HYDROGENATION OF METHIONINE CONTAINING PEPTIDES 131
BENZYLOXYCARBONYL-GLYCYL-L-TRYPTOPHYL-L-METHIONYL-
/?-IERT-BUTYL-L-ASPARTYL-L-PHENYLALANINE AMIDE 131 1.3 TRANSFER
HYDROGENATION WITH 1,4-CYCLOHEXADIENE AS HYDROGEN DONOR 133
A^-TERF-BUTYLOXYCARBONYL-L-LYSYL-O-TERT-BUTYL-L- THREONINE METHYL ESTER
133
2 REDUCTION WITH SODIUM IN LIQUID AMMONIA 135
L-GLUTAMINYL-L-ASPARAGINE 135
3 REMOVAL OF THE PHTHALYL (PHTHALOYL) GROUP BY HYDRAZINOLYSIS 137
GLYCYL-GLYCINE 137
4 ACIDOLYSIS 138
4.1 HYDROBROMIC ACID IN ACETIC ACID 138
GLYCYL-L-PHENYLALANINE BENZYL ESTER HYDROBROMIDE . . 138
S-BENZYL-L-CYSTEINYL-L-PROLYL-L-LEUCYL-GLYCINAMIDE . . . 138 4.2
HYDROBROMIC ACID IN TRIFLUOROACETIC ACID 140
A-MELANOTROPIN 140
IMAGE 8
XVI CONTENTS
4.3 HYDROCHLORIC ACID IN ACETIC ACID 141
NITRO-L-ARGINYL-COPOLYMER 141
4.4 TRIFLUOROACETIC ACID 142
L-METHIONYL-L-GLUTAMINYL-L-HISTIDYL-L-PHENYLALANYL-L-
ARGINYL-L-TRYPTOPHYL-GLYCINAMIDE ACETATE 142
4.5 REMOVAL OF PROTECTING GROUPS WITH TRIFLUOROACETIC ACID-THIOANISOLE
144
PORCINE VASOACTIVE INTESTINAL PEPTIDE 144
4.6 LIQUID HYDROGEN FLUORIDE 145
OXYTOCIN 145
5 HYDROLYSIS 148
5.1 BASE CATALYZED HYDROLYSIS OF ALKYL ESTERS (SAPONIFICATION WITH
ALKALI) 148
IV-BENZYLOXYCARBONYL-S-BENZYL-L-CYSTEINYL-L-TYROSINE. . 148 5.2 ACID
CATALYZED HYDROLYSIS 149
PHTHALYL-L-PHENYLALANYL-GLYCINE 149
5.3 ENZYME CATALYZED HYDROLYSIS 150
5.3.1 ENZYMATIC REMOVAL OF THE PHENYLACETYL GROUP FROM THE E-AMINO GROUP
OF LYSINE RESIDUES. . .. 150 PARTIAL DEPROTECTION OF A DIPEPTIDE
DERIVATIVE . . 150 DESAMINO LYSINE VASOPRESSIN 150
5.3.2 CHYMOTRYPSIN CATALYZED HYDROLYSIS OF ALKYL ESTERS 151
L-PROLYL-L-PHENYLALANINE 151
BENZYLOXYCARBONYL-L-VALYL-L-TYROSINE 152
6 BASE CATALYZED ELIMINATION 153
6.1 REMOVAL OF THE 9-FLUORENYLMETHYLOXYCARBONYL (FMOC) GROUP 153
9-FLUORENYLMETHYLOXYCARBONYL-L-ASPARAGINYL-S-BENZYL-
L-CYSTEINYL-L-PROLYL-L-TRYPTOPHYL-GLYCINAMIDE 153 6.2 CLEAVAGE OF
9-FLUORENYLMETHYL ESTERS 155
L-LEUCYL-L-PHENYLALANINE 155
7 NUCLEOPHILIC DISPLACEMENT 156
7.1 REMOVAL OF THE O-NITROBENZENESULFONYL (NPS) GROUP. . 156
IV -FERT-BUTYLOXYCARBONYL-L-LYSYL-L-LEUCYL-L- PHENYLALANYL-JV E
-FERF-BUTYLOXYCARBONYL-L-LYSYL-IV -TER- BUTYLOXYCARBONYL-L-LYSINE 156
7.2 CLEAVAGE OF 2-TRIMETHYLSILYLETHYL ESTERS WITH FLUORIDES 157
IV-BENZYLOXYCARBONYL-O-TERT-BUTYL-L-THREONINE 157 8 IODOLYSIS 159
REMOVAL OF THE S-TRITYL GROUP BY IODOLYSIS WITH CONCOMITANT OXIDATION TO
THE DISULFIDE 159
9 REDUCTION OF METHIONINE SULFOXIDE CONTAINING PEPTIDES. . . 161
L-PROLYL-L-TYROSYL-IV -TOSYL-L-LYSYL-L-METHIONINE 161
IMAGE 9
CONTENTS XVII
V SPECIAL PROCEDURES 163
1 AMMONOLYSIS OF ESTERS 165
1.1 CONVERSION OF A PEPTIDE ETHYL ESTER TO THE CORRESPONDING AMIDE 165
BENZYLOXYCARBONYL-L-PROLYL-L-LEUCYL-GLYCINAMIDE . . .. 165 1.2
AMMONOLYSIS OF ACTIVE ESTERS 166
BENZYLOXYCARBONYL-L-ASPARAGINE AMIDE 166
2 TRANSESTERIFICATION 167
2.1 CLEAVAGE OF THE ESTER BOND BETWEEN PEPTIDE AND POLYMERIC SUPPORT BY
TRANSESTERIFICATION FOLLOWED BY HYDROLYSIS 167
BENZYLOXYCARBONYL-L-ALANYL-L-PHENYLALANINE 167 3 CYCLIZATION 169
3.1 CYCLIZATION THROUGH THE FORMATION OF A DISULFIDE BOND 169
DESAMINO-OXYTOCIN 169
3.2 RING CLOSURE THROUGH AN AMIDE BOND 170
DITOSYL-GRAMICIDIN S 170
DESTHIOMALFORMIN 171
4 POLYCONDENSATION 173
4.1 JV-CARBOXYANHYDRIDES 173
JV -BENZYLOXYCARBONYL-IV A -CARBOXY-L-LYSINE ANHYDRIDE. 173 4.2
POLY-IV^-BENZYLOXYCARBONYL-L-LYSINE 174
4.3 SYNTHESIS OF SEQUENTIAL PEPTIDES BY POLYCONDENSATION. 175 POLY
(L-LYSYL-L-ALANYL-L-ALANINE) TRIFLUOROACETATE . . .. 175 5 PARTIAL
SYNTHESIS 178
HUMAN INSULIN 178
ZINC FREE INSULIN 178
N A1 ,N M -DI-FERT-BUTYLOXYCARBONYL-B(23-30)-DESOCTA- PEPTIDE INSULIN,
(BOC) 2 -DOI 179
HUMAN INSULIN THROUGH CONDENSATION WITH DICYCLOHEXYLCARBODIIMIDE 179
HUMAN INSULIN VIA ENZYME-CATALYZED COUPLING . . .. 179
VI MODELS FOR THE STUDY OF RACEMIZATION 181
1 BENZOYL-LEUCYL-GLYCINE ETHYL ESTER 183
2 THE ANDERSON-CALLAHAN TEST 184
BENZYLOXYCARBONYL-GLYCYL-L-PHENYLALANYL-GLYCINE ETHYL ESTER 184 3
ACYLATION WITH ACETYL-L-ISOLEUCINE 186
ACETYL-L-ISOLEUCINE 186
IMAGE 10
XVIII CONTENTS
ACETYL-L-ISOLEUCYL-GLYCINE ETHYL ESTER AND ACETYL-D-
ALLOISOLEUCYL-GLYCINE ETHYL ESTER 186
4 THE IZUMIYA-MURAOKA MODEL 189
GLYCYL-ALANYL-LEUCINE 189
5 SYNTHESIS AND ENANTIOSELECTIVE ENZYMIC HYDROLYSIS OF TETRAALANINE 191
VII REAGENTS FOR PEPTIDE SYNTHESIS 193
1 FERF-BUTYL AZIDOFORMATE 195
FERF-BUTYL PHENYL CARBONATE 195
FERF-BUTYL CARBAZATE 195
FERF-BUTYL AZIDOFORMATE 196
2 1-ADAMANTYL CHLOROCARBONATE 197
3 L-ISOBUTYLOXYCARBONYL-2-ISOBUTYLOXY-L,2-DIHYDROQUINOLINE (IIDQ) 198
4 DIPHENYL PHOSPHORAZIDATE (DIPHENYLPHOSPHORYL AZIDE, DPPA) 199
5 3-HYDROXY-3,4-DIHYDROQUINAZOLINE-4-ONE (4-HYDROXYQUINAZOLINE 3-OXIDE)
200
2-AMINOBENZHYDROXAMIC ACID 200
3-HYDROXY-3,4-DIHYDROQUINAZOLINE-4-ONE 200
6 1-HYDROXYBENZOTRIAZOLE 201
7 ETHYL 2-HYDROXIMINO-2-CYANOACETATE 202
8 L-GUANYL-3,5-DIMETHYL-PYRAZOLE NITRATE 203
VIII APPENDIX 205
1 CONVERSION OF DICYCLOHEXYLAMMONIUM SALTS OF PROTECTED AMINO ACIDS TO
THE FREE ACIDS 207
N-O-NITROBENZENESULFONYL-O-TERT-BUTYL-L-THREONINE JTY-HYDROXYSUCCINIMIDE
ESTER 207
2 PREPARATION PF ANALYTICAL SAMPLES 208
2.1 ELEMENTAL ANALYSIS 208
2.2 AMINO ACID ANALYSIS 208
2.3 NMR SPECTRA 210
SUBJECT INDEX 211
|
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| author | Bodanszky, Miklos Bodanszky, Agnes |
| author_facet | Bodanszky, Miklos Bodanszky, Agnes |
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| author_sort | Bodanszky, Miklos |
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| building | Verbundindex |
| bvnumber | BV009524214 |
| callnumber-first | Q - Science |
| callnumber-label | QD431 |
| callnumber-raw | QD431 |
| callnumber-search | QD431 |
| callnumber-sort | QD 3431 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 8560 |
| classification_tum | CHE 820f |
| ctrlnum | (OCoLC)29843611 (DE-599)BVBBV009524214 |
| dewey-full | 547.7/56 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.7/56 |
| dewey-search | 547.7/56 |
| dewey-sort | 3547.7 256 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | 2., rev. ed. |
| format | Book |
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| id | DE-604.BV009524214 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T17:36:30Z |
| institution | BVB |
| isbn | 3540575057 0387575057 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-006289078 |
| oclc_num | 29843611 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-29T DE-703 DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-83 DE-188 |
| owner_facet | DE-355 DE-BY-UBR DE-29T DE-703 DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-83 DE-188 |
| physical | XVIII, 217 S. graph. Darst. |
| publishDate | 1994 |
| publishDateSearch | 1994 |
| publishDateSort | 1994 |
| publisher | Springer |
| record_format | marc |
| series2 | Springer lab manual |
| spelling | Bodanszky, Miklos Verfasser aut The practice of peptide synthesis M. Bodanszky ; A. Bodanszky 2., rev. ed. Berlin u.a. Springer 1994 XVIII, 217 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Springer lab manual Peptides - Synthèse Produtos naturais (quimica organica) larpcal Peptides Synthesis Methode (DE-588)4038971-6 gnd rswk-swf Peptidsynthese (DE-588)4173715-5 gnd rswk-swf Peptidsynthese (DE-588)4173715-5 s Methode (DE-588)4038971-6 s 1\p DE-604 Bodanszky, Agnes Verfasser aut SWB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006289078&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 |
| spellingShingle | Bodanszky, Miklos Bodanszky, Agnes The practice of peptide synthesis Peptides - Synthèse Produtos naturais (quimica organica) larpcal Peptides Synthesis Methode (DE-588)4038971-6 gnd Peptidsynthese (DE-588)4173715-5 gnd |
| subject_GND | (DE-588)4038971-6 (DE-588)4173715-5 |
| title | The practice of peptide synthesis |
| title_auth | The practice of peptide synthesis |
| title_exact_search | The practice of peptide synthesis |
| title_full | The practice of peptide synthesis M. Bodanszky ; A. Bodanszky |
| title_fullStr | The practice of peptide synthesis M. Bodanszky ; A. Bodanszky |
| title_full_unstemmed | The practice of peptide synthesis M. Bodanszky ; A. Bodanszky |
| title_short | The practice of peptide synthesis |
| title_sort | the practice of peptide synthesis |
| topic | Peptides - Synthèse Produtos naturais (quimica organica) larpcal Peptides Synthesis Methode (DE-588)4038971-6 gnd Peptidsynthese (DE-588)4173715-5 gnd |
| topic_facet | Peptides - Synthèse Produtos naturais (quimica organica) Peptides Synthesis Methode Peptidsynthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006289078&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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