Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/5767
Title: Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
Authors: Silva, M. Manuel Cruz 
Riva, Sergio 
Melo, M. Luísa Sá e 
Issue Date: 2004
Citation: Tetrahedron: Asymmetry. 15:7 (2004) 1173-1179
Abstract: Stereoisomerically pure 3[beta]-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for [alpha]- and [beta]-epoxidation of [Delta]5-unsaturated steroids with enzymatic stereoselective esterification of the 3[beta]-hydroxyl group. 5[beta],6[beta]-Epoxy-3[beta]-hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5[alpha],6[alpha]-epoxy-3[beta]-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3[beta]-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.
URI: http://hdl.handle.net/10316/5767
Rights: openAccess
Appears in Collections:FFUC- Artigos em Revistas Internacionais

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