A. Janoski, F. C. Shulman, G. Wright
1974
Citations
0
Influential Citations
65
Citations
Journal
Steroids
Abstract
Abstract The direct one-step synthesis of 3-(O-carboxymethyl)oximes of representative C21-4-pregnen-3,20-diones is reported. The method requires the preparation of a 3-enamine derivative which, serving as an intermediate product, is readily converted to the 3-(O-carboxymethyl)oxime upon addition of one molar equivalent of O-(carboxymethyl)hydroxylamine hemihydrochloride. The reaction appears to be generally applicable for selective 3-(O-carboxymethyl)oxime formation in steroids possessing multi-carbonyl groups, thus facilitating the coupling of steroidal haptens to protein at the C-3 position of the steroid molecule for enhanced immunospecificity. In this manner, antisera to 16α-hydroxyprogesterone and 17α-hydroxy-progesterone were obtained from immunized rabbits and specificity was established by radioimmunoassay.