Pseudomonas cepacia lipase shows opposite stereoselectivity in the acylation versus the deacylation of diastereoisomeric 1-O- and 3-O-β-D-glycopyranosyl-sn-glycerols: while the 2,3,4,6-tetraacetylated 1-O-glycosyl-sn-glycerols were the preferred substrates in the former reaction, the 3-O-peracetylated derivatives were hydrolyzed in the latter one. In this way, both 1-O- and 3-O-stereoisomers could be obtained optically pure as residual substrates.
Optically pure 1-O- and 3-O-β-D-glucosyl- and galactosyl-sn-glycerols through lipase-catalyzed transformations / D. Colombo, F. Ronchetti, A. Scala, I. Taino, F. Albini, L. Toma. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 36:27(1995), pp. 4865-4868. [10.1016/0040-4039(95)00840-9]
Optically pure 1-O- and 3-O-β-D-glucosyl- and galactosyl-sn-glycerols through lipase-catalyzed transformations
D. ColomboPrimo
;F. RonchettiSecondo
;A. Scala;
1995
Abstract
Pseudomonas cepacia lipase shows opposite stereoselectivity in the acylation versus the deacylation of diastereoisomeric 1-O- and 3-O-β-D-glycopyranosyl-sn-glycerols: while the 2,3,4,6-tetraacetylated 1-O-glycosyl-sn-glycerols were the preferred substrates in the former reaction, the 3-O-peracetylated derivatives were hydrolyzed in the latter one. In this way, both 1-O- and 3-O-stereoisomers could be obtained optically pure as residual substrates.
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