2-O-(β-D-Glucopyranosyl)glycerol and 2-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl]glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) Upases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol using LCA fiunished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.

Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols / D. Colombo, F. Ronchetti, A. Scala, I. Taino, F. Albini, L. Toma. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 5:7(1994), pp. 1377-1384. [10.1016/0957-4166(94)80181-9]

Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols

D. Colombo
Primo
;
F. Ronchetti
Secondo
;
A. Scala;
1994

Abstract

2-O-(β-D-Glucopyranosyl)glycerol and 2-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl]glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) Upases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol using LCA fiunished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/176944
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