Enantioselective enzymatic aminolysis of a racemic 2-isoxazolylacetate alkyl ester

Pseudomonas cepacia lipase or Candida antartica lipase B catalyzes the enantioselective aminolysis of a racemic 2-isoxazolylacetate alkyl ester, isobutyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate, by 3-amino-N-(butoxycarbonyl)-L-alanine methyl ester, mono(4-methylbenzenesulfonate) to pro...

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Bibliographic Details
Published in:Canadian Journal of Chemistry
Main Authors: Sigmund, Amy E, McNulty, Kenneth C, Nguyen, Dzuy, Silverman, Charlotte E, Ma, Philip, Pesti, Jaan A, DiCosimo, Robert
Format: Article in Journal/Newspaper
Language:English
Published: Canadian Science Publishing 2002
Subjects:
Organic Chemistry
General Chemistry
Catalysis
antartic*
Online Access:http://dx.doi.org/10.1139/v02-004
http://www.nrcresearchpress.com/doi/pdf/10.1139/v02-004
Description
Summary:Pseudomonas cepacia lipase or Candida antartica lipase B catalyzes the enantioselective aminolysis of a racemic 2-isoxazolylacetate alkyl ester, isobutyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate, by 3-amino-N-(butoxycarbonyl)-L-alanine methyl ester, mono(4-methylbenzenesulfonate) to produce the corresponding amide, (R)-methyl-3-[[[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-L-alanine, which is an intermediate in the preparation of an isoxazoline-based platelet glycoprotein IIb/IIIa antagonist. Key words: enantioselective aminolysis, Pseudomonas cepacia lipase, Candida antartica lipase B.

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