REGIOSELECTIVE ESTERIFICATION OF POLYHYDROXYLATED STEROIDS BY CANDIDA-ANTARCTICA LIPASE-B

Authors
BERTINOTTI A CARREA G OTTOLINA G RIVA S
Citation
A. Bertinotti et al., REGIOSELECTIVE ESTERIFICATION OF POLYHYDROXYLATED STEROIDS BY CANDIDA-ANTARCTICA LIPASE-B, Tetrahedron, 50(46), 1994, pp. 13165-13172
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
46
Year of publication
1994
Pages
13165 - 13172
Database
ISI
SICI code
0040-4020(1994)50:46<13165:REOPSB>2.0.ZU;2-E
Abstract
The regioselectivity of Candida antarctica lipase B towards the acetyl ation of polyhydroxylated steroids has been systematically investigate d. The enzyme showed a marked preference for the alcoholic moieties on the A ring and on the steroid side chain, making it possible the sele ctive acylation at the positions 3 or 21 of polyhydroxy steroids. Acyl ation with the synthetically useful esters chloroacetate and levulinat e was also accomplished, whereas esterification with benzoate and piva loate was unsuccessful.