Enantioselective transesterifications of 2-methyl-1-alcohols catalysed by lipases from Pseudomonas

• Published in: Tetrahedron: asymmetry Vol. 5; no. 5; pp. 785 - 788
• Main Authors: Nordin, On, Hedenström, Erik, Högberg, Hans-Erik
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.05.1994; Elsevier; Elsevier Science
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; Organic chemistry; Physical Sciences; Science & Technology; WATER ACTIVITY; PHEROMONE; PS; KINETIC RESOLUTIONS; REDUCTION; ORGANIC-SOLVENTS; BLOCKS; ENANTIOMERS; ESTERIFICATION; Pseudomonadales; Five membered ring; Enzyme; Aliphatic compound; Triacylglycerol lipase; Esterases; Transesterification; Pseudomonas; Carboxylic ester hydrolases; Primary alcohol; Organic solvent; Sulfur heterocycle; Optical resolution; Medium effect; Bacteria; Hydrolases; Pseudomonadaceae; Enantiomeric excess; Kinetics
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(00)86227-8

Racemic β-methyl-2-thiophenepropanol was resolved ( E ≈ 200) via transesterification catalysed by lipase from Pseudomonas flourescens using an excess of vinyl acetate in chloroform at an initial water activity: a w = 0.32. When trying to resolve rac-2-methyl-l-alkanols more modest E values were obtained ( E ≈ 10) and were of the same older of magnitude irrespective of substrate chainlength, water activity, immobilization, acyl donor or other Pseudomonas derived lipases. However, the reaction rates are affected by variations of these parameters. Both the rates and E-values were influenced by the nature of the solvent Enantioselective transesterification of 2-methyl-1-alcohols. Influence of water activity, solvent, substrate, acyl donor and immobilization.