Steroidal oxime methyl esters

Table 11 Lipase-Mediated Diastereoselective Hydrolysis of Steroidal Oxime Methyl Esters ...

Steroids Biie acids Fatty acids Urinary acids Ketones Prostagiandins Oximes, TMS, t-BDMS ethers Methyl esters, TMS ethers Methyl esters, TMS, t-BDMS esters Methyl esters, TMS, t-BDMS esters Oximes Methyl esters, oximes, TMS, ethers Steroid profiles Liver disease, peroxisomal deficiencies Phospholipids, triglycerides Acidurias, diabetes Diabetes Healing processes, pain... 

Geometrical isomeric mixtures of steroidal oxime esters have been evaluated for the enzymatic transformations. In this respect, the work by Adamczyk and co-workers [27] describes the use of lipase from CCL in the diastereoselective hydrolysis of 3-(0-carbox-ymethyl)oxime methyl esters, 17a-hydroxyprogesterone 122, progesterone 124, testosterone 126, and cortisol 128. CCL proved to be effective in carrying out hydrolysis of methyl esters of steroidal 3-carboxymethyl oximes in a mild manner affording the E and Z dia-stereoisomers 123/122, 125/124, 127/126, and 129/128 in different ratios. The enzyme exhibited a preference for the anti isomer (Table 11). The faster rate and greater selectivity observed for 128 is probably due to the cortisol derivative s better solubility in the reaction media. 

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