The 2,4-dimethylpent-3-yloxycarbonyl (Doc) group as a new, nucleophile-resistant protecting group for tyrosine in solid phase peptide synthesis

被引：10

作者：

Rosenthal, K ^{[1
]}

Karlstrom, A ^{[1
]}

Unden, A ^{[1
]}

机构：

[1] UNIV STOCKHOLM, DEPT NEUROCHEM & NEUROTOXICOL, S-10691 STOCKHOLM, SWEDEN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

基金：

瑞典研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02471-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,4-dimethylpent-3-yloxycarbonyl (Dec) group is presented as a new protecting group for tyrosine. The Doc group is 1000-fold more stable towards the nucleophile piperidine than the commonly used 2-bromobenzyloxycarbonyl (2-BrZ) group is, and it is completely cleaved by hydrogen fluoride. (C) 1997, Elsevier Science Ltd.

引用

页码：1075 / 1078

页数：4

共 9 条

[1] ACID STABILITY OF SEVERAL BENZYLIC PROTECTING GROUPS USED IN SOLID-PHASE PEPTIDE SYNTHESIS - REARRANGEMENT OF 0-BENZYLTYROSINE TO 3-BENZYLTYROSINE
ERICKSON, BW
MERRIFIELD, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) : 3750 - 3756
[2] A new protecting group for aspartic acid that minimizes piperidine-catalyzed aspartimide formation in Fmoc solid phase peptide synthesis
Karlstrom, A
Unden, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4243 - 4246
[3] KARLSTROM A, 1996, J CHEM SOC CHEM COMM, P959
[4] KARLSTROM A, IN PRESS INT J PEPT
[5] KARLSTROM A, 1996, J CHEM SOC CHEM COMM, P1471
[6] THE BETA-2,4-DIMETHYL-3-PENTYL ESTER AS A NEW PROTECTING GROUP FOR ASPARTIC-ACID THAT PREVENTS BASE-CATALYZED ASPARTIMIDE FORMATION IN SOLID-PHASE PEPTIDE-SYNTHESIS
KARLSTROM, AH
UNDEN, AE
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3909 - 3912
[7] STEWART JM, 1981, PEPTIDES, V3, P169
[8] Tam J., 1987, PEPTIDES, V9, P185
[9] PROTECTION OF TYROSINE IN SOLID-PHASE PEPTIDE SYNTHESIS
YAMASHIRO, D
LI, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (03) : 591 - 592

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