ALDOTETROSES AND C(3)-MODIFIED ALDOHEXOSES AS SUBSTRATES FOR N-ACETYLNEURAMINIC ACID ALDOLASE - A MODEL FOR THE EXPLANATION OF THE NORMAL AND THE INVERSED STEREOSELECTIVITY

被引：54

作者：

FITZ, W ^{[1
]}

SCHWARK, JR ^{[1
]}

WONG, CH ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 12期

关键词：

D O I：

10.1021/jo00117a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase. C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition. Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions. The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.

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页码：3663 / 3670

页数：8

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