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

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 obta...

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Published inTetrahedron: asymmetry Vol. 5; no. 5; pp. 785 - 788
Main Authors Nordin, On, Hedenström, Erik, Högberg, Hans-Erik
Format Journal Article
LanguageEnglish
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
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Abstract 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.
AbstractList Racemic beta-methyl-2-thiophenepropanol was resolved (E approximate to 200) via transesterification catalysed by lipase from Pseudomonas fluorescens using an excess of vinyl acetate in chloroform at an initial water activity: a(W) = 0.32. When trying to resolve rac-2-methyl-1-alkanols more modest E-values were obtained (E approximate to 10) and were of the same order 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.
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.
Author Hedenström, Erik
Högberg, Hans-Erik
Nordin, On
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Issue 5
Keywords 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
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PublicationTitle Tetrahedron: asymmetry
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Elsevier
Elsevier Science
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Snippet Racemic β-methyl-2-thiophenepropanol was resolved ( E ≈ 200) via transesterification catalysed by lipase from Pseudomonas flourescens using an excess of vinyl...
Racemic beta-methyl-2-thiophenepropanol was resolved (E approximate to 200) via transesterification catalysed by lipase from Pseudomonas fluorescens using an...
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SubjectTerms 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
Title Enantioselective transesterifications of 2-methyl-1-alcohols catalysed by lipases from Pseudomonas
URI https://dx.doi.org/10.1016/S0957-4166(00)86227-8
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