Selective 3-(O-carboxymethyl)oxime formation in steroidal 3,20-diones for hapten immunospecificity |
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Authors: | A H Janoski F C Shulman G E Wright |
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Affiliation: | 1. Department of Medicine, University of Maryland School of Medicine Baltimore, Maryland, 21201 USA;2. Department of Pathology, University of Maryland School of Medicine Baltimore, Maryland, 21201 USA;3. Department of Medicinal Chemistry, University of Maryland School of Pharmacy Baltimore, Maryland, 21201 USA |
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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. |
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Keywords: | Reprint requests are to be forwarded to A. H. Janoski M.D. University of Maryland Hospital Department of Medicine Division of Endocrinology 22 South Greene Street Baltimore Md. 21201. |
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