Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 625-628

  Ema, Tadashi ^a   Maeno, Soichi ^a   Takaya, Yusuke ^a   Sakai, Takashi ^a   Utaka, Masanori ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; ESTER DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; ENANTIOMER; ENZYME ACTIVITY; ESTERIFICATION; PRIORITY JOURNAL;

EID: 0029915768     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00049-3     Document Type: Article

References (30)

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24. Solvent effect was investigated using isopropenyl acetate and vinyl butyrate. The plots of the E values against the logP values of solvents gave bell-shaped curves having a peak maximum around logP ∼ 1 in both cases. See also ref. 3a.
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26. Recent X-ray chrystallographic studies have revealed that several lipases have a catalytic triad in the active site. (a) Brady, L.; Brzozowski, A. M.; Derewenda, Z. S.; Dodson, E.; Dodson, G.; Tolley, S.; Turkenburg, J. P.; Christiansen, L.; Huge-Jensen, B.; Norskov, L.; Thim, L.; Menge, U. Nature, 1990, 343, 767.
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28. It has recently been reported that in nonaqueous media such as isooctane the rates of the lipase-catalyzed esterification of the longer carboxylic acids were faster. Okahata, Y.; Fujimoto, Y.; Ijiro, K. J. Org. Chem. 1995, 60, 2244.
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30. To check the effect of the concentration, we performed a preparative resolution of rac-1 using vinyl acetate under the same reaction conditions as those in the kinetic measurements, with the result that the E value was enhanced up to 147.