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

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 dias...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: D. Colombo, F. Ronchetti, A. Scala, I. Taino, F. Albini, L. Toma
Format: Article in Journal/Newspaper
Language:English
Published: 1994
Subjects:
Settore BIO/10 - Biochimica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/176944
https://doi.org/10.1016/0957-4166(94)80181-9
Description
Summary: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.

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