Enzymatic Preparation of (R)-3-Hydroxy-2-Methylpropyl Butyrate by Asymmetric Hydrolysis
- 1 January 1990
- journal article
- research article
- Published by Taylor & Francis in Biocatalysis
- Vol. 3 (1-2) , 159-167
- https://doi.org/10.3109/10242429008992058
Abstract
(R)-3-Hydroxy-2-methylpropyl butyrate was formed by asymmetric hydrolysis of the corresponding prochiral diester with lipase P (Amano) in high enantiomeric excess. Various physical and chemical reaction parameters were altered in order to optimize the stereoselectivity of the enzymatic reaction; low temperature (0d`C) combined with the application of salting-in salts or (polyhydric) alcohols turned out to be the most suitable systems providing the monobutyrate in 96% ee. Attempts towards chiral monobutyrate by enzymatic esterification of the corresponding prochiral diol were unsuccessful.Keywords
This publication has 13 references indexed in Scilit:
- Enantioselektive Verseifung der Diacetate von 2‐Nitro‐1,3‐diolen mit Schweineleber‐Esterase und Herstellung enantiomerenreiner Derivate von 2‐Nitro‐allylalkoholen (chirale Verknüpfungsreagenzien)Helvetica Chimica Acta, 1988
- Enantiomerenreine glycerin-derivate durch enzymatische hydrolyse prochiraler ester 1)Tetrahedron Letters, 1987
- Penicillinacylase and α-chymotrypsin catalysed hydrolysis of phenylacetate and phenylpropionate esters of 2,2-dimethyl-1,3-dioxolane-4-methanolsJournal of the Chemical Society, Chemical Communications, 1987
- Synthesis of both enantiomeric forms of 2-substituted 1,3-propanediol monoacetates starting from a common prochiral precursor, using enzymatic transformations in aqueous and in organic mediaTetrahedron Letters, 1986
- Enzymes in asymmetric synthesis: Effect of reaction media on the PLE catalysed hydrolysis of diestersTetrahedron Letters, 1986
- Immobilized porcine liver esterase: a convenient reagent for the preparation of chiral building blocks.Tetrahedron Letters, 1985
- Stereospecific Hydrolysis of 2-Oxazolidinone Esters and Separation of Products with an Immobilized Lipase ColumnAgricultural and Biological Chemistry, 1985
- Stereospecific hydrolysis by soluble and immobilized lipasesBiotechnology & Bioengineering, 1982
- Synthetic studies on (2R,4'R,8'R)-.alpha.-tocopherol. An approach utilizing side chain synthons of microbiological originThe Journal of Organic Chemistry, 1976
- The Hydrogenation of Esters to Alcohols at 25-150°Journal of the American Chemical Society, 1948