Enhancing enantioselectivity of a lipid-coated lipase via imprinting methods for esterification in organic solvents

Yoshio Okahata, Akihiko Hatano, Kuniharu Ijiro

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Lipase OF from Candida showed only low enantioselectivity for esterification of (R)- or S-1-phenylethanol with lauric acid ( vR vS = 5.5). However, when lipase OF was imprinted with a substrate analogue such as (R)-1-phenylethanol and then coated with synthetic glycolipid molecules, the imprinted lipid-coated lipase shows a large enantioselectivity for the esterification in anhydrous isooctane ( vR vS = 77). When the native lipase OF was imprinted by the same procedure, the enantioselectivity hardly changed. The lipid coating was important to keep the imprinted structure as well as to solubilize enzymes in organic solvents. The improved enantioselectivity was confirmed from Michaelis-Menten kinetics as due to the intramolecular catalytic reaction and not the substrate binding process. The improved enantioselectivity reverts to the original non-imprinted value if kept in the organic solvents at high temperatures for days.

Original languageEnglish
Pages (from-to)1311-1322
Number of pages12
JournalTetrahedron: Asymmetry
Volume6
Issue number6
DOIs
Publication statusPublished - 1995
Externally publishedYes

Fingerprint

Enantioselectivity
Lipases
Esterification
Lipase
Organic solvents
Lipids
lipids
lauric acid
enzymes
analogs
coatings
acids
kinetics
Candida
Glycolipids
molecules
Substrates
Enzymes
Coatings
Molecules

ASJC Scopus subject areas

  • Catalysis
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Enhancing enantioselectivity of a lipid-coated lipase via imprinting methods for esterification in organic solvents. / Okahata, Yoshio; Hatano, Akihiko; Ijiro, Kuniharu.

In: Tetrahedron: Asymmetry, Vol. 6, No. 6, 1995, p. 1311-1322.

Research output: Contribution to journalArticle

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