V. Pouzar et I. Cerny, PREPARATION OF (17E)-3-BETA-HYDROXYANDROST-5-EN-17-ONE (O-CARBOXYMETHYL)OXIME DERIVATIVES WITH SHORT PEPTIDE-CHAIN .376., Collection of Czechoslovak Chemical Communications, 59(9), 1994, pp. 2042-2056
17-(O-Carboxymethyl)oxime (CMO) derivatives of 3 beta-acetoxy-, 3 beta
-methoxymethoxy-, 3 beta-hydroxyandrost-5-en-17-one, and of -androst-4
-ene-3,17-dione (IV - VI, XXIX) were prepared. Methods for the attachm
ent of amino acids to the CMO group and for the peptide chain elongati
on were tested. The mixed anhydride method was used for linking the fi
rst amino acid unit (Gly, beta Ala, or Gly-Gly dipeptide), further uni
ts were added by the N-hydroxysuccinimide method. Compounds with one t
o four amino acids were prepared. This concept is suitable for the pre
paration of haptens with variable bridge length for the binding studie
s.