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Do enzymes recognis...
Do enzymes recognise remotely located stereocentres? : Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
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- Hedenström, Erik (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Nguyen, Ba-Vu (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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Silks III, L. A. (author)
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(creator_code:org_t)
- 2002
- 2002
- English.
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In: Tetrahedron. - 0957-4166 .- 1362-511X. ; 13:8, s. 835-844
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- lipase-catalysed esterification
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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