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

共 11 条

[1] BECK WS, 1982, B12, V2, P9
[2] VITAMIN B12 IN PISUM SATIVUM (L.)
FRIES, L
[J]. PHYSIOLOGIA PLANTARUM, 1962, 15 (03) : 566 - &
[3] CHEMISTRY OF THE TROPANE ALKALOIDS .34. 1,2-MIGRATION OF HYDROGEN DURING THE BIOSYNTHESIS OF TROPIC ACID FROM PHENYLALANINE
LEETE, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) : 7271 - 7272
[4] USE OF C-13 NUCLEAR MAGNETIC-RESONANCE TO ESTABLISH THAT BIOSYNTHESIS OF TROPIC ACID INVOLVES AN INTRAMOLECULAR REARRANGEMENT OF PHENYLALANINE
LEETE, E
KOWANKO, N
NEWMARK, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) : 6826 - 6830
[5] BIOGENESIS OF HYOSCYAMINE
LEETE, E
MARION, L
SPENSER, ID
[J]. NATURE, 1954, 174 (4431) : 650 - 651
[6] LEETE E, 1973, PHYTOCHEMISTRY, V11, P1713
[7] PLANT PROANTHOCYANIDINS .8. BIOSYNTHESIS OF FLAVAN-3-OLS AND OTHER SECONDARY PLANT-PRODUCTS FROM (2S)-PHENYLALANINE
PLATT, RV
OPIE, CT
HASLAM, E
[J]. PHYTOCHEMISTRY, 1984, 23 (10) : 2211 - 2217
[8] POSTON JM, 1978, PHYTOCHEMISTRY, V17, P401, DOI 10.1016/S0031-9422(00)89324-3
[9] RETEY J, 1982, NEW COMPREHENSIVE BI, V3, P261
[10] ABSOLUTE CONFIGURATION OF TROPIC ACID
WATSON, MB
YOUNGSON, GW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (12): : 1597 - &

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