Porcine pancreatic, Candida cylindracea, and Pseudomonas fluorescens lipases, suspended in organic solvents, were used to regioselectively acylate methyl α-L- and α-D-rhamnopyranoside and methyl α-L- and α-D-fucopyranoside. While the D-sugars always gave the 2-butyrate as the main product, their L enantiomers showed a different regioselectivity; however, by proper selection of the enzyme, in the L series the rather unreactive 4-OH function could be preferentially acylated.
REGIOSELECTIVE ACYLATION OF 6-DEOXY-L-HEXOSIDES AND 6-DEOXY-D-HEXOSIDES THROUGH LIPASE-CATALYZED TRANSESTERIFICATION - ENHANCED REACTIVITY OF THE 4-OH FUNCTION IN THE L SERIES / P. CIUFFREDA, D. COLOMBO, F. RONCHETTI, L. TOMA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 55:13(1990), pp. 4187-4190. [10.1021/jo00300a042]
REGIOSELECTIVE ACYLATION OF 6-DEOXY-L-HEXOSIDES AND 6-DEOXY-D-HEXOSIDES THROUGH LIPASE-CATALYZED TRANSESTERIFICATION - ENHANCED REACTIVITY OF THE 4-OH FUNCTION IN THE L SERIES
P. CiuffredaPrimo
;D. ColomboSecondo
;F. RonchettiPenultimo
;
1990
Abstract
Porcine pancreatic, Candida cylindracea, and Pseudomonas fluorescens lipases, suspended in organic solvents, were used to regioselectively acylate methyl α-L- and α-D-rhamnopyranoside and methyl α-L- and α-D-fucopyranoside. While the D-sugars always gave the 2-butyrate as the main product, their L enantiomers showed a different regioselectivity; however, by proper selection of the enzyme, in the L series the rather unreactive 4-OH function could be preferentially acylated.
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