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Issue 91, 2014
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The perils of rational design – unexpected irreversible elimination of fluoride from 3-fluoro-2-methylacyl-CoA esters catalysed by α-methylacyl-CoA racemase (AMACR; P504S)

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Abstract

α-Methylacyl-CoA racemase (AMACR; P504S) catalyses ‘racemization’ of 2-methylacyl-CoAs, the activation of R-ibuprofen and is a promising cancer drug target. Human recombinant AMACR 1A catalyses elimination of 3-fluoro-2-methyldecanoyl-CoAs to give E-2-methyldec-2-enoyl-CoA and fluoride anion, a previously unknown reaction. ‘Racemization’ of 2-methyldec-3-enoyl-CoAs was also catalysed, without double bond migration.

Graphical abstract: The perils of rational design – unexpected irreversible elimination of fluoride from 3-fluoro-2-methylacyl-CoA esters catalysed by α-methylacyl-CoA racemase (AMACR; P504S)

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The article was received on 05 Aug 2014, accepted on 18 Sep 2014 and first published on 18 Sep 2014


Article type: Communication
DOI: 10.1039/C4CC06127F
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Chem. Commun., 2014,50, 14164-14166

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    The perils of rational design – unexpected irreversible elimination of fluoride from 3-fluoro-2-methylacyl-CoA esters catalysed by α-methylacyl-CoA racemase (AMACR; P504S)

    M. Yevglevskis, G. L. Lee, M. D. Threadgill, T. J. Woodman and M. D. Lloyd, Chem. Commun., 2014, 50, 14164
    DOI: 10.1039/C4CC06127F

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