Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
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.
Hedenstroem, Erik,Nguyen, Ba-Vu,Silks III, Louis A.
p. 835 - 844
(2007/10/03)
6,12-dimethylpentadecan-2-one and its use in monitoring and controlling the banded cucumber beetle
A pheromonal compound produced by the banded cucumber beetle has been identified as 6,12-dimethylpentadecan-2-one. Both the synthetically prepared racemic compound and the purified natural pheromone elicited responses by banded cucumber males in field tests. By attracting adult beetles to field traps, this compound is a useful tool for the monitoring and controlling of this major agricultural pest.
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(2008/06/13)
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