Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Reexamination Certificate
2006-04-11
2006-04-11
Lilling, Herbert J. (Department: 1651)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
C435S156000, C435S280000
Reexamination Certificate
active
07026144
ABSTRACT:
A process of separating a single desired stereoisomer from a racemic mixture of eight stereoisomers of a compound of formula (III), wherein R1represents an isopropanol group, an isopropyl group or an isopropylene group, includes the steps of: contacting the racemic mixture in a suitable organic solvent with an esterifying agent and a stereospecific enzyme which stereoselectively esterifies the —OH group of the desired stereoisomer, for a time sufficient to convert a desired percentage of the desired stereoisomer to a compound of formula (IV), wherein R1is as defined above and R4is an alkyl or an aryl group, to give a first reaction product including the compound of formula (IV), the organic solvent, the unconverted stereoisomers of the compound of formula (III), excess esterifying agent and by-products of the reaction; and separating the compound of formula (IV) from the first reaction product. The process is of particular application for the production of (−)-menthol
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Langrand et al “Lipase-catalyzed ester formation in organic solvents an easy preparative resolution of alpha-substuted cyclohexanols” Tetrahedron Letters vol. 26, No. 15 pp 1857-1860 1985.
Shimada et al “Enzymatic Synthesis of L-menthyl esters in organic solvent-free system” JAOCS vol. 76 No. 10 pp 1139-1142 (1999).
Cambou et al “Preparative Production of Optically Active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media” Jour American Chem Society vol. 106, No. 9 pp 2687-2692 1984.
Cernia, E. et al., The Role of the Reaction Medium in Lipase-catalyzed Esterifications and Transesterifications; Chemistry and Physics of Lipids, vol. 93 (1998); p. 157-168.
Brady Dean
Chaplin Jennifer Ann
Evans-Dickson Melanie Daryl
Gardiner Neil Stockenstrom
Marais Stephanus Francois
CSIR
Lilling Herbert J.
Sterne Kessler Goldstein & Fox P.L.L.C.
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