Solid phase synthesis of C-terminal carbohydrate modified enkephalins

被引：42

作者：

Drouillat, B ^{[1
]}

Kellam, B ^{[1
]}

Dekany, G ^{[1
]}

Starr, MS ^{[1
]}

Toth, I ^{[1
]}

机构：

[1] UNIV LONDON,SCH PHARM,DEPT PHARMACEUT & BIOL CHEM,LONDON WC1N 1AX,ENGLAND

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1997年 / 7卷 / 17期

基金：

英国惠康基金;

关键词：

D O I：

10.1016/S0960-894X(97)00395-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

1-Azido-2,3,4-tri-O-acetyl-beta-D-glucuronic acid (1), immobilised on 2-chlorotrityl and NovaSyn TGR resin, was efficiently reduced to its corresponding resin bound glycosyl amine (3) using propane-1,3-dithiol and triethylamine. Subsequent acylation of (3) with (1), generated the carbohydrate dimer (4). In addition, Fmoc based peptide syntheses performed on (3) and (4) afforded the C-terminal modified Leu and Met-enkephalins (7-10). Preliminary pharmacological evaluation of these compounds identified glycopeptide (7) as a potent and selective delta-opioid receptor agonist. (C) 1997 Elsevier Science Ltd.

引用

页码：2247 / 2250

页数：4

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