Primary allenic alcohols of high optical purity via lipase catalyzed resolution

The lipase from Candida rugosa lipase (CRL) was used for the preparation of optically active primary allenic alcohols with axial chirality. The biocatalytic material used was the commercial CRL (C-CRL) and propan-2-ol-treated CRL (PT-CRL). The kinetic resolution of (±)- 1 and (±)- 3a– c in water usi...

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Bibliographic Details
Published inJournal of molecular catalysis. B, Enzymatic Vol. 17; no. 6; pp. 261 - 266
Main Authors Cipiciani, Antonio, Bellezza, Francesca
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 17.07.2002
Elsevier Science
Subjects
Allenic alcohols
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Candida rugosa
Enantioselectivity
Fundamental and applied biological sciences. Psychology
Lipases
Methods. Procedures. Technologies
Allenic alcohols
Enantioselectivity
Lipases
Candida rugosa
Enzyme
Triacylglycerol lipase
Enzymatic catalysis
Esterases
Carboxylic ester hydrolases
Primary alcohol
Fungi
Optical resolution
Hydrolases
Fungi Imperfecti
Allenic compound
Thallophyta
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Summary:The lipase from Candida rugosa lipase (CRL) was used for the preparation of optically active primary allenic alcohols with axial chirality. The biocatalytic material used was the commercial CRL (C-CRL) and propan-2-ol-treated CRL (PT-CRL). The kinetic resolution of (±)- 1 and (±)- 3a– c in water using C-CRL resulted in either the absence of or low enantiomeric ratio, whereas PT-CRL increased the E-value. Under optimized conditions (temperature and medium used) (+)- S- 3a and (−)- R- 4 were isolated in excellent yields and high optical purity (o.p.). The resolution was carried out on multigram scale in water/ n-hexane at 4 °C.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(02)00043-7