SYNTHESES OF 15α- AND 15β-CARBOXYMETHYLTESTOSTERONE BOVINE SERUM ALBUMIN CONJUGATES: CHARACTERISTICS OF THE ANTISERA TO TESTOSTERONE

Article abstract of DOI:10.1016/0039-128X(82)90037-X

Syntheses of 15α- and 15β-carboxymethyltestosterone (15α- and 15β-CMT) were investigated in order to prepare testosterone-bovine serum albumin conjugates for radioimmunoassay of testosterone.A mixture of 15α- and 15β-bis(ethoxycarbonyl)methyl-3β-hydroxy-5-androsten-17-one (IIa and IIb) obtained by reaction of 3β-hydroxy-5,15-androstadien-17-one (I) and sodium diethyl malonate was oxidized to afford a mixture of 15α- and 15β-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione (Va and Vb).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 15α- and 15β-CMT.The antisera, generated in rabbits by immunization with the bovine serum albumin (BSA) conjugates of 15α- and 15β-CMT, respectively, exhibited high specificity for testosterone.