SYNTHESIS OF POTENTIAL INHIBITORS OF HEMAGGLUTINATION BY INFLUENZA-VIRUS - CHEMOENZYMIC PREPARATION OF N-5 ANALOGS OF N-ACETYLNEURAMINIC ACID

被引：44

作者：

SPARKS, MA ^{[1
]}

WILLIAMS, KW ^{[1
]}

LUKACS, C ^{[1
]}

SCHRELL, A ^{[1
]}

PRIEBE, G ^{[1
]}

SPALTENSTEIN, A ^{[1
]}

WHITESIDES, GM ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON | 1993年 / 49卷 / 01期

关键词：

CHEMOENZYMIC SYNTHESIS; NEURAMINIC ACID; N-ACYL NEURAMINIC ACID; INFLUENZA VIRUS; HEMAGGLUTINATION INHIBITORS;

D O I：

10.1016/S0040-4020(01)80502-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymic route to neuraminic acid 2 is described. This method is based on conversion of N-carbobenzoxymannosamine (ManCBz) 3 to N-carbobenzaxyneuraminic acid (Neu5CBz) 4, catalyzed by Neu5Ac aldolase. The Neu5CBz 4 was converted to the alpha-methyl glycoside 8 and deprotected to afford the free amine 2. This procedure has been scaled up to generate 10-gram quantities of 2. N-Acylation of 2 produced several new N-acyl neuraminic acid analogs; these have been evaluated as inhibitors of adhesion of influenza virus to chicken erythrocytes in a hemagglutination inhibition assay (HAI). This preparation of neuraminic acid 2 is compared with other literature procedures.

引用

页码：1 / 12

页数：12

共 43 条

[1] THE NEURAMINIDASE OF INFLUENZA-VIRUS [J].