Unexpected stereoselective exchange of straight-chain fatty acyl-CoA alpha-protons by human alpha-methylacyl-CoA racemase 1A (P504S)
- PMID: 20442897
- DOI: 10.1039/c002509g
Unexpected stereoselective exchange of straight-chain fatty acyl-CoA alpha-protons by human alpha-methylacyl-CoA racemase 1A (P504S)
Abstract
Alpha-methylacyl-CoA racemase (AMACR; P504S) catalysed exchange of straight-chain fatty acyl-CoA alpha-protons. One alpha-proton was removed in each catalytic cycle, with the pro-S proton preferred. This reaction was most efficient for straight-chain substrates with longer side-chains. 2-Methyldecanoyl-CoA underwent alpha-proton exchange 3x more efficiently (as judged by K(cat)/K(m)) than decanoyl-CoA.
Similar articles
-
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).Chem Commun (Camb). 2014 Nov 25;50(91):14164-6. doi: 10.1039/c4cc06127f. Chem Commun (Camb). 2014. PMID: 25277991
-
Synthesis and use of isotope-labelled substrates for a mechanistic study on human alpha-methylacyl-CoA racemase 1A (AMACR; P504S).Org Biomol Chem. 2009 Feb 7;7(3):543-52. doi: 10.1039/b815396e. Epub 2008 Nov 28. Org Biomol Chem. 2009. PMID: 19156321
-
The catalysis of the 1,1-proton transfer by alpha-methyl-acyl-CoA racemase is coupled to a movement of the fatty acyl moiety over a hydrophobic, methionine-rich surface.J Mol Biol. 2007 Apr 6;367(4):1145-61. doi: 10.1016/j.jmb.2007.01.062. Epub 2007 Jan 27. J Mol Biol. 2007. PMID: 17320106
-
Discovery and clinical application of a novel prostate cancer marker: alpha-methylacyl CoA racemase (P504S).Am J Clin Pathol. 2004 Aug;122(2):275-89. doi: 10.1309/EJUY-UQPE-X1MG-68MK. Am J Clin Pathol. 2004. PMID: 15323145 Review.
-
α-Methylacyl-CoA racemase (AMACR): metabolic enzyme, drug metabolizer and cancer marker P504S.Prog Lipid Res. 2013 Apr;52(2):220-30. doi: 10.1016/j.plipres.2013.01.001. Epub 2013 Jan 29. Prog Lipid Res. 2013. PMID: 23376124 Review.
Cited by
-
Molecular basis of acyl-CoA ester recognition by α-methylacyl-CoA racemase from Mycobacterium tuberculosis.J Biol Chem. 2025 Jul;301(7):110302. doi: 10.1016/j.jbc.2025.110302. Epub 2025 May 29. J Biol Chem. 2025. PMID: 40447188 Free PMC article.
-
High-throughput screen identifies novel inhibitors of cancer biomarker α-methylacyl coenzyme A racemase (AMACR/P504S).Mol Cancer Ther. 2011 May;10(5):825-38. doi: 10.1158/1535-7163.MCT-10-0902. Epub 2011 Mar 25. Mol Cancer Ther. 2011. PMID: 21441411 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Miscellaneous