2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity
1993 (English)In: Tetrahedron Asymmetry, ISSN 09574166 (ISSN), Vol. 4, no 8, 1869-1878 p.Article in journal (Refereed) Published
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 Â± 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.
2 methyldecanoic acid, 2 methyldecanol, alkanol, carboxylic acid derivative, unclassified drug, article, candida, drug purification, enantiomer, enzyme activity
IdentifiersURN: urn:nbn:se:kth:diva-74875DOI: 10.1016/S0957-4166(00)80427-9OAI: oai:DiVA.org:kth-74875DiVA: diva2:490135
Correspondence Address: Hogberg, H.-E.; Department of Chemistry, Univ. College of Sundsvall/Harnosand, S-851 70 Sundsvall, Sweden NR 201408052012-02-032012-02-032012-02-03Bibliographically approved