PMID: 11325269Apr 28, 2001Paper

Molecular basis for enantioselectivity of lipase from Chromobacterium viscosum toward the diesters of 2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol

The Journal of Organic Chemistry
D G GascoyneRomas J Kazlauskas

Abstract

2,3-Dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol, 1, is a chiral bisphenol useful for preparation of polymers. Previous screening of commercial hydrolases identified lipase from Chromobacterium viscosum (CVL) as a highly regio- and enantioselective catalyst for hydrolysis of diesters of 1. The regioselectivity was > or =30:1 favoring the ester at the 5-position, while the enantioselectivity varied with acyl chain length, showing the highest enantioselectivity (E = 48 +/- 20 S) for the dibutanoate ester. In this paper, we use a combination of nonsymmetrical diesters and computer modeling to identify that the remote ester group controls the enantioselectivity. First, we prepared nonsymmetrical diesters of (+/-)-1 using another regioselective, but nonenantioselective, reaction. Lipase from Candida rugosa (CRL) showed the opposite regioselectivity (>30:1), allowing removal of the ester at the 4'-position (the remote ester in the CVL-catalyzed reaction). Regioselective hydrolysis of (+/-)-1-dibutanoate (150 g) gave (+/-)-1-5-dibutanoate (89 g, 71% yield). Acylation gave nonsymmetrical diesters that varied at the 4'-position. With no ester at the 4'-position, CVL showed no enantioselectivity, while hindered esters (3,3-...Continue Reading

References

Sep 1, 1995·Trends in Biochemical Sciences·O B Ptitsyn
May 23, 1996·Nature·R W HooftE E Abola

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Citations

Nov 4, 2006·Bioprocess and Biosystems Engineering·Wei-Guo ZhangQing-Xun Song
Dec 17, 2002·Current Opinion in Biotechnology·Uwe T Bornscheuer
Mar 12, 2002·Bioorganic & Medicinal Chemistry·R V MuralidharP Nigam
Jun 1, 2002·Current Opinion in Chemical Biology·Manfred T Reetz
Jul 28, 2006·Trends in Biotechnology·Paolo BraiucaLucia Gardossi
Feb 24, 2006·Chembiochem : a European Journal of Chemical Biology·Iván LavanderaVicente Gotor
Mar 31, 2004·Biotechnology and Bioengineering·Francesco SecundoMarina Lotti
Sep 22, 2001·Science·R Kazlauskas

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