Stereoselective enzymatic hydrolysis of (exo,exo)-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol diacetate ester in a biphasic system

A key chiral intermediate lactol(3)(3aS (3a alpha ,4 alpha ,7 alpha ,7a alpha ))-hexahydro-4,7-epoxy-isobenzofuran-1 (3H)-one was prepared for the total synthesis of a new thromboxane antagonist. The stereoselective hydrolysis of (exo,exo)-7-oxabicyclo(2.2.1)heptane-2,3-dimethanol, diacetate ester (...

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Bibliographic Details
Published in:Applied microbiology and biotechnology 1992-05, Vol.37 (2), p.180-183
Main Authors: PATEL, R. N, LIU, M, AMIT BANERJEE, SZARKA, L. J
Format: Article
Language:English
Subjects:
(exo,exo)-7-oxabicyclo(2.2.1)heptane-2,3-dimethanol
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Fundamental and applied biological sciences. Psychology
hydrolysis
immobilized enzymes
Methods. Procedures. Technologies
Pseudomonas
stereochemistry
stereoselectivity
triacylglycerol lipase
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Summary:A key chiral intermediate lactol(3)(3aS (3a alpha ,4 alpha ,7 alpha ,7a alpha ))-hexahydro-4,7-epoxy-isobenzofuran-1 (3H)-one was prepared for the total synthesis of a new thromboxane antagonist. The stereoselective hydrolysis of (exo,exo)-7-oxabicyclo(2.2.1)heptane-2,3-dimethanol, diacetate ester (1) to the corresponding chiral monoacetate ester (2) was carried out with lipases, among which Amano P-30 lipase from Pseudomonas sp. was most effective since it gave the desired enantiomer of monoacetate ester. A yield of 75 mol% and optical purity of >99% was obtained when the reaction was conducted in a biphasic system with 10% toluene at 5 g/l of the substrate. Lipase P-30 was immobilized on Accurel polypropylene (PP) and the immobilized enzyme was reused (five cycles) without loss of enzyme activity, productivity or optical purity.
ISSN:0175-7598
1432-0614
DOI:10.1007/BF00178167