Prostaglandin chemistry—IV : Microbiological kinetic resolution and asymmetric hydrolysis of 3,5-diacetoxycyclopent-1-ene |
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Authors: | S Miura S Kurozumi T Toru T Tanaka M Kobayashi S Matsubara S Ishimoto |
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Institution: | Teijin Institute for Biomedical Research, 4-3-2 Asahigaoka, Hino, Tokyo 191, Japan |
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Abstract: | A 1:1 mixture of cis- and trans-3,5-diacetoxycyclopent-1-ene (1) was asymmetrically hydrolysed by baker's yeast to give trans-3(R)-acetoxy-5(R)-hydroxycyclopent-1-ene (R-2a) and S-predominant 3,5-dihydroxycyclopent-1-ene (3) accompanied by trans-3(R),5(R)-diacetoxycyclopent-1-ene (R-1a).The optical activities on the products were found to be dependent on the difference of the enzymatic hydrolytic rate among cis-, trans(S,S)- and trans(R,R)-3,5-diacetoxycyclopent-1-ene.The asymmetric hydrolysis was also investigated on wheat germ lipase, citrus acetyl esterase, and the lipase prepared from Aspergillus niger. |
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