SYNTHESES OF 15-ALPHA-CARBOXYMETHYLTESTOSTERONE AND 15-BETA-CARBOXYMETHYLTESTOSTERONE BOVINE SERUM-ALBUMIN CONJUGATES - CHARACTERISTICS OF THE ANTISERA TO TESTOSTERONE

被引:15
作者
MIYAKE, Y
KUBO, Y
IWABUCHI, S
KOJIMA, M
机构
关键词
D O I
10.1016/0039-128X(82)90037-X
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
Syntheses of 15.alpha.- and 15.beta.-carboxymethyltestosterone (15.alpha.- and 15.beta.-CMT) were investigated to prepare testosterone-bovine serum albumin conjugates for radioimmunoassays of testosterone. A mixture of 15.alpha.- and 15.beta.-bis(ethoxycarbonyl)methyl-3.beta.-hydroxy-5-androstein-17-one obtained by a reaction of 3.beta.-hydroxy-5,15-androstadien-17-one and sodium diethyl malonate was oxidized to afford a mixture of 15.alpha.- and 15.beta.-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione. After the separation by silica gel chromatography, each epimer obtained was hydrolyzed by acid, followed by decarboxylation, and selective reduction of the 17-ketone to give 15.alpha.- and 15.beta.-CMT. The antisera, generated in rabbits by immunization with the bovine serum albumin conjugates of 15.alpha.- and 15.beta.-CMT, respectively, exhibited high specificity for testosterone.
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页码:245 / 259
页数:15
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