(p-sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-selectin glycoprotein ligand 1 (PSGL-1)

被引：10

作者：

Herzner, Holger ^{[1
]}

Kunz, Horst ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 28期

关键词：

D O I：

10.1016/j.tet.2007.03.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6423 / 6436

页数：14

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