Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-143-50 Peptide

被引：30

作者：

Ali, Ahmed M. ^{[1
]}

Hill, Bryan ^{[1
]}

Taylor, Scott D. ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

SOLID-PHASE SYNTHESIS; DERIVATIVES; INHIBITORS; RECEPTOR; ACIDS;

D O I：

10.1021/jo900122c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.

引用

页码：3583 / 3586

页数：4

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