DIASTEREOSELECTIVE SYNTHESIS OF PHYCOCYANOBILIN CYSTEINE ADDUCTS

被引：38

作者：

BISHOP, JE ^{[1
]}

NAGY, JO ^{[1
]}

OCONNELL, JF ^{[1
]}

RAPOPORT, H ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 21期

关键词：

D O I：

10.1021/ja00021a032

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methodology is presented for the synthesis of two diastereomers of a cysteine-linked phycocyanobilin derivative. The crucial reaction is a diastereoselective 1,6-Michael addition of cysteine methyl ester to an appropriate dihydropyrromethenone educt. The diastereomers so generated were then elaborated to two phycocyanobilin trimethyl esters. Definitive assignments of relative stereochemistry, double bond geometry, and solution conformation are accomplished by application of ROESY NMR experiments, while absolute stereochemical assignments are based on degradation to compounds of known chirality.

引用

页码：8024 / 8035

页数：12

共 42 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].