SYNTHESIS OF 3-ALPHA,6-BETA,7-ALPHA,12-BETA-TETRAHYDROXY-5-BETA-CHOLANOIC AND 3-ALPHA,6-BETA,7-BETA,12-BETA-TETRAHYDROXY-5-BETA-CHOLANOIC ACIDS

被引：7

作者：

AGGARWAL, SK

BATTA, AK

SALEN, G

SHEFER, S

机构：

[1] UNIV MED & DENT NEW JERSEY,NEW JERSEY MED SCH,SAMMY DAVIS JR LIVER CTR,NEWARK,NJ 07103

[2] UNIV MED & DENT NEW JERSEY,NEW JERSEY MED SCH,DEPT MED,NEWARK,NJ 07103

[3] VET ADM MED CTR,E ORANGE,NJ 07019

来源：

STEROIDS | 1992年 / 57卷 / 03期

关键词：

STEROIDS; TETRAHYDROXY BILE ACIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; STEROLS;

D O I：

10.1016/0039-128X(92)90067-J

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Chemical synthesis of 3-alpha,6-beta,7-alpha,12-beta- and 3-alpha,6-beta,7-beta,12-beta-tetrahydroxy-5-beta-cholan-24-oic acids is described. 3-alpha,12-beta-Dihydroxy-5-beta-chol-6-en-24-oic acid used as the starting material in the synthesis was prepared via oxidation of 3-alpha,12-alpha-dihydroxy-5-beta-chol-6-en-24-oic acid 3-hemisuccinate at C-12 followed by reduction with potassium/tertiary amyl alcohol. alpha-Epoxidation of the ester diacetate of 3-alpha,12-beta-dihydroxy-5-beta-chol-6-en-24-oic acid with m-chloroperbenzoic acid followed by cleavage of the epoxide with acetic acid and alkaline hydrolysis yielded 3-alpha,6-beta,7-alpha,12-beta-tetrahydroxy-5-beta-cholan-24-oic acid (overall yield 25%). N-Methylmorpholine-N-oxide-catalyzed osmium tetroxide oxidation of the ester diacetate of 3-alpha,12-beta-dihydroxy-5-beta-chol-6-en-24-oic acid followed by alkaline hydrolysis yielded 3-alpha,6-beta,7-beta,12-beta-tetrahydroxy-5-beta-cholan-24-oic acid (overall yield 33%). The structures of the synthesized bile acids were confirmed from their proto nuclear magnetic resonance and mass spectral fragmentation patterns.

引用

页码：107 / 111

页数：5

共 19 条

[1] ANALYSIS OF BILE-ACID GLUCURONIDES IN URINE - IDENTIFICATION OF 3-ALPHA,6-ALPHA,12-ALPHA-TRIHYDROXY-5-BETA-CHOLANOIC ACID [J].