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2-Methylalkanoic ac...
2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa : Alcohol chain length and enantioselectivity
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- Berglund, Per (author)
- Department of Chemistry, University College of Sundsvall/Härnösand S-851 70 Sundsvall, Sweden
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- Holmquist, Mats Torsten (author)
- KTH,Biokemi och biokemisk teknologi
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- Hedenstrom, Erik (author)
- Department of Chemistry, University College of Sundsvall/Härnösand S-851 70 Sundsvall, Sweden
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- Hult, Karl (author)
- KTH,Biokemi och biokemisk teknologi
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- Hogberg, Hans-Erik (author)
- Department of Chemistry, University College of Sundsvall/Härnösand S-851 70 Sundsvall, Sweden
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(creator_code:org_t)
- 1993
- 1993
- English.
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In: Tetrahedron Asymmetry. - 0957-4166. ; 4:8, s. 1869-1878
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- 2 methyldecanoic acid
- 2 methyldecanol
- alkanol
- carboxylic acid derivative
- unclassified drug
- article
- candida
- drug purification
- enantiomer
- enzyme activity
Publication and Content Type
- ref (subject category)
- art (subject category)
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