Journal ArticleDOI
Problems of Acyl Migration in Lipase-Catalyzed Enantioselecttve Transformation of Meso-1,3-Diol Systems
Kevin Liu,Kenji Nozaki,Chi-Huey Wong +2 more
- Vol. 3, pp 169-177
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TLDR
The acyl migration was not observed in the enantioselective transesterification of meso-1,3-diols in neutral organic solvents and a mechanism of the migration has been proposed to proceed through a six-member ring transition that accounts for the experimental results.Abstract:
In the enantioselective hydrolysis of the di-O-acetyl derivatives of meso-1,3-diol catalyzed by lipases, racemization of the monoacetate products occurs due to non-enzymatic general base-catalyzed acyl migration. The rate of acyl migration increases with increase of pH and buffer concentration. A mechanism of the migration has been proposed to proceed through a six-member ring transition that accounts for the experimental results. The acyl migration, however, was not observed in the enantioselective transesterification of meso-1,3-diols in neutral organic solvents.read more
Citations
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Journal ArticleDOI
Lipase-catalyzed syntheses of monoacylglycerols
TL;DR: The application of lipases for the production of monoacylglycerols is reviewed in this article, where reaction systems ranging from organic solvents to reverse micelles and solid-phase systems are covered, including examples for the continuous production of partial glycerides.
Journal ArticleDOI
Lipase-catalyzed transesterification in organic solvents: Applications to the preparation of enantiomerically pure compounds
TL;DR: An overview of the state of the art through examples chosen from the most recent literature is offered, focusing mainly on the preparation of enantiomerically pure products which can be formed by this enzymatic approach.
Journal ArticleDOI
Acyl group migrations in 2-monoolein
TL;DR: Acyl migration in 2-monoolein dissolved in solvents under conditions common in lipid modification reactions has been studied in this article, where the effects on acyl migration of solvent, incubation temperature, water activity, polar additives and solid additives have been investigated.
Journal ArticleDOI
Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme Catalysis
TL;DR: Results indicate that the major part of the meso product is formed via an intramolecular acyl-transfer pathway, making efficient use of all the diol material.
References
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Journal ArticleDOI
Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics
TL;DR: In this article, a lipase-catalyzed transesterification of the prochiral symmetric dialcohol (I) in an organic medium yields the optically active monoacetate (S)-(III) together with the diacetate(IV), making the process irreversible and simpler for product isolation.
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A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase
TL;DR: In this article, pig liver esterase-(PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicar boxylic acid, and diacids with a prochiral center, was studied with 14 substrates.
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Bifunctional chiral synthons via biochemical methods. III. Optical purity enhancement in enzymic asymmetric catalysis
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Enzymes in organic synthesis. 35. Stereoselective pig liver esterase catalyzed hydrolyses of 3-substituted glutarate diesters. Optimization of enantiomeric excess via reaction conditions control
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Lipase-catalyzed irreversible transesterification for preparative synthesis of chiral glycerol derivatives
Yi Fong Wang,Chi Huey Wong +1 more
TL;DR: In this paper, a synthese de derives acyles of meso-1,3-diols enantiomeres, utilisant cette technique de transesterification irreversible catalysee par une lipase, is presented.