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Enantioselective Hydrolysis of d,l ‐Menthyl Benzoate to L ‐(–)‐Menthol by Recombinant Candida rugosa Lipase LIP1
Author(s) -
Vorlová Sandra,
Bornscheuer Uwe T.,
Gatfield Ian,
Hilmer JensMichael,
Bertram HeinzJuergen,
Schmid Rolf D.
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200212)344:10<1152::aid-adsc1152>3.0.co;2-n
Subject(s) - candida rugosa , chemistry , enantioselective synthesis , lipase , menthol , hydrolysis , organic chemistry , stereoselectivity , enantiomeric excess , enantiomer , biocatalysis , catalysis , enzyme , reaction mechanism
The stereoselective synthesis of L ‐menthol is an attractive process in the flavor and fragrance industry. One promising way to obtain optically pure menthol is the enantioselective hydrolysis of menthol esters under enzymatic catalysis. We developed an effective and highly enantioselective method for the synthesis of L ‐(−)‐menthol (>99% EE) by hydrolyzing the key industrial starting compound, d, l ‐menthyl benzoate. The enzyme of choice was the lipase from Candida rugosa (CRL). While commercially available preparations of this lipase showed only minor selectivity ( E =15), excellent enantiomeric purity ( E >100) was achieved using the heterologously expressed isoenzyme LIP1.