Tetrahedron: Asymmetry

Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2-to 8-methyldecanoic acids

E Hedenström, BV Nguyen, LA Silks

Index: Hedenstroem, Erik; Nguyen, Ba-Vu; Silks III, Louis A. Tetrahedron Asymmetry, 2002 , vol. 13, # 8 p. 835 - 844

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Citation Number: 31

Abstract

Several racemic methyl decanoic acids have been synthesised and successfully resolved in esterification with 1-hexadecanol at aw= 0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E= 2.8–68) obtained were surprisingly high even when the methyl group was as remotely located as in 8- methyldecanoic acid (E= 25). Interestingly, the lipase shows enantiopreference for the S- ...