Homochiral glycerol derivatives by lipase-catalysed racemate resolution.
Various aspects of enzyme-catalysed racemate resolution are discussed by using examples from hydrolysis of butanoates of glycerol derivatives. Primary esters of various 1,2-ketals gave low enantioselectivity (E). The results with secondary esters varied. The highest E value (> 100) was obtained when the primary ether groups were methyl and phenylethyl. For the corresponding methyl, phenyl diether E was observed to increase as the hydrolysis proceeded. The stereochemistry of the products agree with a proposed model for lipases.
Department of Chemistry, University of Trondheim, Norway.
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Waagen
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Partali
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Hansen
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Anthonsen
D002087:Butyrates / Q000737:chemistry* / Q000378:metabolism; D020148:Butyric Acid; D005990:Glycerol / Q000031:analogs & derivatives* / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis; D013237:Stereoisomerism; D013379:Substrate Specificity
D002087:Butyrates; D004364:Pharmaceutical Preparations; D020148:Butyric Acid; D008049:Lipase; D005990:Glycerol