CHEMISTRY OF THE TROPANE ALKALOIDS .35. STEREOCHEMISTRY OF THE 1,2-MIGRATION OF THE CARBOXYL GROUP THAT OCCURS DURING THE BIOSYNTHESIS OF TROPIC ACID FROM PHENYLALANINE

被引：25

作者：

LEETE, E

机构：

[1] Natural Products Laboratory, School of Chemistry, University of Minnesota, Minneapolis,MN,55455, United States

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1987年 / 65卷 / 01期

关键词：

Amino acids - Biochemistry;

D O I：

10.1139/v87-036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(2S,3R)- and (2S,3,S)-[1-14C,3-3H]phenylalanine were fed in separate experiments to Datura innoxia plants. The distribution of isotopes in the resultant labeled hyoscyamine and scopolamine indicates that the biosynthesis of the acid moiety of these ester alkaloids, namely (S)-tropic acid, involves the migration of the carboxyl group of phenylalanine to its prochiral C-3 position with retention of configuration.

引用

页码：226 / 228

页数：3

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