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)

Yevglevskis, Maksims, Lee, Guat L., Threadgill, Michael D., Woodman, Timothy J. and Lloyd, Matthew D. 2014. 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). Chemical Communications 50 (91) , pp. 14164-14166. 10.1039/C4CC06127F

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1359-7345
Date of Acceptance:	18 September 2014
Last Modified:	15 Jul 2021 01:11
URI:	https://orca.cardiff.ac.uk/id/eprint/132988

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