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2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity
Mid Sweden University.ORCID iD: 0000-0002-9577-832X
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1993 (English)In: Tetrahedron Asymmetry, ISSN 09574166 (ISSN), Vol. 4, no 8, 1869-1878 p.Article in journal (Refereed) Published
Abstract [en]

Enantiomerically pure (R)-2-methyldecanoic acid and (S)-2-methyl-1-decanol were prepared in a multi gram scale by esterification reactions catalysed by lipase from Candida rugosa. The enantiomeric ratios (E-values) were determined as a function of the chain length of the alcohol used as the complementary substrate in cyclohexane. In the resolution of 2-methyldecanoic acid the highest value (E = 37 ± 5) was obtained, when either 2-hexanol, 1-heptanol or 1-octanol were used. In contrast, when resolving 2-methyloctanoic acid, the E-values increased continually with increasing chain length of the alcohol used. 1-Hexadecanol gave the highest value: E > 100. The E-values were determined from the enantiomeric excess (ee) of the product at a conversion below 0.4. After two consecutive esterification reactions enantiomerically pure (R)-2-methyldecanoic acid, >99.8% ee, and after subsequent reduction of the ester produced, (S)-2-methyl-1-decanol, 96.7% ee, were obtained.

Place, publisher, year, edition, pages
1993. Vol. 4, no 8, 1869-1878 p.
Keyword [en]
2 methyldecanoic acid, 2 methyldecanol, alkanol, carboxylic acid derivative, unclassified drug, article, candida, drug purification, enantiomer, enzyme activity
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-74875DOI: 10.1016/S0957-4166(00)80427-9OAI: diva2:490135
Correspondence Address: Hogberg, H.-E.; Department of Chemistry, Univ. College of Sundsvall/Harnosand, S-851 70 Sundsvall, Sweden NR 20140805Available from: 2012-02-03 Created: 2012-02-03 Last updated: 2012-02-03Bibliographically approved

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Berglund, P.
Organic Chemistry

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