Stereochemical control in the preparation of α-amino N-methylthiazolidine masked aldehydes used for peptide aldehydes synthesis

被引：11

作者：

Gros, C ^{[1
]}

Boulègue, C ^{[1
]}

Galeotti, N ^{[1
]}

Niel, G ^{[1
]}

Jouin, P ^{[1
]}

机构：

[1] CNRS, CCIPE, UPR9023, F-34094 Montpellier 5, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 13期

关键词：

N-trityl; thiazolidine; peptide aldehyde; solid phase; ligation;

D O I：

10.1016/S0040-4020(02)00115-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral N-methyl thiazolidines masked alpha-amino aldehydes are used for solid phase peptide aldehyde elongation. Contrary to N-Boc-protected alpha-amino aldehydes, N-trityl protection secures the chiral integrity of the incoming aldehyde chiral Cl' carbon atom during condensation of the amino aldehydes with L-cysteinyl residues. The Ac-Tyr-Val-Ala-Asp-H caspase inhibitor was prepared on a solid support starting from the N-trityl-amino thiazolidine masked aspartinal as a validation of this process. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2673 / 2680

页数：8

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[1] IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES [J].