ANTIBODY CATALYSIS OF A DISFAVORED CHEMICAL TRANSFORMATION

被引：156

作者：

JANDA, KD ^{[1
]}

SHEVLIN, CG ^{[1
]}

LERNER, RA ^{[1
]}

机构：

[1] SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

SCIENCE | 1993年 / 259卷 / 5094期

关键词：

D O I：

10.1126/science.8424171

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Organic reactions are often limited by stereoelectronic constrains that appear along the reaction coordinate. An antibody has been generated that overcomes these constraints and catalyzes a highly disfavored chemical transformation. The antibody facilitates the difficult 6-endo-tet ring closure of an epoxy-alcohol to form a tetrahydropyran. The catalyzed process is in formal violation of what has become known as Baldwin's rules for ring-closure reactions. In addition to controlling the regiochemistry of the disfavored cyclization reaction, these catalytic antibodies resolve enantiomeric substrates to afford a stereochemically pure product. The principles demonstrated in this study may be applicable to other disfavored chemical processes.

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页码：490 / 493

页数：4

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