Preparation of (17E)-3β-Hydroxyandrost-5-en-17-one (O-Carboxymethyl)oxime Derivatives with Short Peptide Chain

Abstract

17-(O-Carboxymethyl)oxime (CMO) derivatives of 3β-acetoxy-, 3β-methoxymethoxy-, 3β-hydroxyandrost-5-en-17-one, and of -androst-4-ene-3,17-dione (IV - VI, XXIX) were prepared. Methods for the attachment of amino acids to the CMO group and for the peptide chain elongation were tested. The mixed anhydride method was used for linking the first amino acid unit (Gly, βAla, or Gly-Gly dipeptide), further units were added by the N-hydroxysuccinimide method. Compounds with one to four amino acids were prepared. This concept is suitable for the preparation of haptens with variable bridge length for the binding studies.