Synthesis of flavor and fragrance esters using Candida antarctica lipase.
Candida antarctica lipase fraction B (CAL-B) showed substrate specificity in the synthesis of esters in hexane involving reactions of short-chain acids having linear (acetic and butyric acids) and branched chain (isovaleric acid) structures, an unsaturated (tiglic acid) fatty acid, and phenylacetic acid with n-butanol and geraniol. The variation in the conversion to the esters was ca. 10%. Similar results were observed in a study of the alcohol specificity of the enzyme for esterification of acetic and butyric acids with four alcohols: n-butyl, isopentyl, 2-phenylethyl, and geraniol. Enantioselectivity of CAL-B in hexane with a range of chiral alpha-substituted or beta-substituted carboxylic acids and n-butyl alcohol was analyzed. The results show that CAL-B can be employed as a robust biocatalyst in esterification reactions due to the high conversions obtained in the synthesis of short-chain flavor esters in an organic solvent, although this enzyme exhibited modest enantioselectivity with chiral short-chain carboxylic acids.
Larios
Araceli
A
Instituto Tecnológico de Veracruz, UNIDA, Av. Miguel A. de Quevedo 2779, 91897, Veracruz, Ver., Mexico.
García
Hugo S
HS
Oliart
Rosa María
RM
Valerio-Alfaro
Gerardo
G
D020001:1-Butanol / Q000378:metabolism; D000085:Acetates / Q000378:metabolism; D000080462:Acyclic Monoterpenes; D001709:Biotechnology / Q000379:methods*; D002087:Butyrates / Q000378:metabolism; D002175:Candida / Q000201:enzymology*; D002264:Carboxylic Acids / Q000378:metabolism; D003437:Crotonates / Q000378:metabolism; D004951:Esterification; D004952:Esters / Q000378:metabolism*; D005421:Flavoring Agents / Q000378:metabolism*; D045782:Hemiterpenes; D006586:Hexanes / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D010421:Pentanoic Acids / Q000378:metabolism; D000439:Pentanols / Q000378:metabolism; D010476:Perfume / Q000378:metabolism*; D010648:Phenylacetates / Q000378:metabolism; D010626:Phenylethyl Alcohol / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity; D013729:Terpenes / Q000378:metabolism
D000085:Acetates; D000080462:Acyclic Monoterpenes; D002087:Butyrates; D002264:Carboxylic Acids; D003437:Crotonates; D004952:Esters; D005421:Flavoring Agents; D045782:Hemiterpenes; D006586:Hexanes; D010421:Pentanoic Acids; D000439:Pentanols; D010476:Perfume; D010648:Phenylacetates; D013729:Terpenes; C008216:isovaleric acid; D020001:1-Butanol; C029683:isopentyl alcohol; D008049:Lipase; C025136:phenylacetic acid; C009489:tiglic acid; C007836:geraniol; D010626:Phenylethyl Alcohol