title: Syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase B from Candida antarctica.
abstract: The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol, (±)-5-methylhexan-2-ol, (±)-octan-2-ol, (±)-heptan-3-ol and (±)-oct-1-en-3-ol. The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.
authors: Institute of Chemistry of São Carlos, University of São Paulo, Av. Trabalhador São-carlense 400, 13560-970 São Carlos, SP, Brazil.
authors: Hercules V
authors: HV
authors: Ferreira
authors: Lenilson C
authors: LC
authors: Rocha
authors: Richele P
authors: RP
authors: Severino
authors: André L M
authors: AL
authors: Porto
mesh_terms: D000085:Acetates / Q000737:chemistry / Q000302:isolation & purification*; D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D004951:Esterification; D005233:Fatty Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D005656:Fungal Proteins / Q000737:chemistry*; D006586:Hexanes / Q000737:chemistry; D008049:Lipase / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000085:Acetates; D005233:Fatty Alcohols; D005656:Fungal Proteins; D006586:Hexanes; D012997:Solvents; D014753:Vinyl Compounds; D008049:Lipase; C431349:lipase B, Candida antarctica; C011566:vinyl acetate