N-in-cyclohexyloxycarbonyl group as a new protecting group for tryptophan

被引：17

作者：

Nishiuchi, Y ^{[1
]}

Nishio, H ^{[1
]}

Inui, T ^{[1
]}

Kimura, T ^{[1
]}

Sakakibara, S ^{[1
]}

机构：

[1] PEPTIDE INST INC,PROT RES FDN,MINO,OSAKA 562,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 42期

关键词：

D O I：

10.1016/0040-4039(96)01691-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new protecting groups were introduced at the N-in-position of tryptophan, and their reactivities were examined under the conditions used for peptide synthesis by Boc-strategy. Among them, the cyclohexyloxycarbonyl (Hoc) group was found to be the most suitable in terms of stability during elongation of the peptide chain and removability at the final HF reaction without resorting to the use of thiols. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7529 / 7532

页数：4

共 9 条

[1] FUJII N, 1984, CHEM PHARM BULL, V32, P2660
[2] DIMERIZATION OF TRYPTOPHAN DERIVATIVES IN TRIFLUOROACETIC-ACID
HASHIZUME, K
SHIMONISHI, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (12) : 3806 - 3810
[3] HASKELLLUEVANO C, 1994, LETT PEPT SCI, V1, P163
[4] PROTECTION OF THE TRYPTOPHAN INDOLE RING IN PEPTIDE-SYNTHESIS - USE OF A NEW DERIVATIVE, N-IN-2,2,2-TRICHLOROETHOXYCARBONYLTRYPTOPHAN
KISO, Y
INAI, M
KITAGAWA, K
AKITA, T
[J]. CHEMISTRY LETTERS, 1983, (05) : 739 - 742
[5] CROWN ETHERS AS CATALYSTS OF FLUORIDE-ANION-MEDIATED REACTIONS IN PEPTIDE-SYNTHESIS .1. PROTECTION OF TRYPTOPHAN BY BENZYLOXYCARBONYL AND 2,4-DICHLOROBENZYLOXYCARBONYL GROUPS
KLAUSNER, YS
CHOREV, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (06): : 627 - 631
[6] MATSUEDA GR, 1982, INT J PEPT PROT RES, V20, P26
[7] SN2 DEPROTECTION OF SYNTHETIC PEPTIDES WITH A LOW CONCENTRATION OF HF IN DIMETHYL SULFIDE - EVIDENCE AND APPLICATION IN PEPTIDE-SYNTHESIS
TAM, JP
HEATH, WF
MERRIFIELD, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) : 6442 - 6455
[8] TAMAMURA H, 1995, CHEM PHARM BULL, V43, P12, DOI 10.1248/cpb.43.12
[9] CYCLIC TAUTOMERS OF TRYPTOPHANS AND TRYPTAMINES .4. SYNTHESIS OF CYCLIC TAUTOMERS OF TRYPTOPHANS AND TRYPTAMINES
TANIGUCHI, M
HINO, T
[J]. TETRAHEDRON, 1981, 37 (08) : 1487 - 1494

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