PREPARATION AND PROPERTIES OF 3-(O-(2-CARBOXYETHYL))OXIME DERIVATIVESOF STEROID-HORMONES

Minerals of 3E and 3Z isomers of 3-(O-(2-carboxyethyl))oxime (CEO) der ivatives of testosterone and 17 alpha-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers Mer e separated after conversion into methyl esters, and mild alkaline hyd rolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosteron e and 17 alpha-methyltestosterone. By the same method, after oximation , methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave ( 3E,20R)-20-hydroxgpregn-4-en-3-one, 3(O-(2-carboxyethyl))oxime and (3Z ,20R)-20-hydroxypregn-4-en-3-one 3-(O-(2-carboxyerhyl))oxime methyl es ters. The oxidation and subsequent hydrolysis of these compounds produ ced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E/ Z-isomers of 3-CEO derivatives are designed for the development of imm unoanalytical systems, which make use of the bridge heterology based o n the geometric isomerism.