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Do enzymes recognise remotely located stereocentres?: Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Responsible organisation
2002 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 13, no 8, 835-844 p.Article in journal (Refereed) Published
Abstract [en]

Several racemic methyl decanoic acids have been synthesised and successfully resolved in esterification with 1-hexadecanol at aw=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids.

Place, publisher, year, edition, pages
2002. Vol. 13, no 8, 835-844 p.
Keyword [en]
lipase-catalysed esterification
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-5189DOI: 10.1016/S0957-4166(02)00172-6ISI: 000176081600007Scopus ID: 2-s2.0-0037095037Local ID: 1861OAI: oai:DiVA.org:miun-5189DiVA: diva2:30221
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-25Bibliographically approved

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CiteExportLink to record
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Citation style
  • apa
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