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Chemical Compound Review

capryl-CoA     [(2R,3S,4R,5R)-5-(6- aminopurin-9-yl)-2...

Synonyms: Decanoyl-coa, CHEBI:28493, D5269_SIGMA, C10:0-CoA, AC1L4VHP, ...
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Disease relevance of Decanoyl-coenzyme A


High impact information on Decanoyl-coenzyme A

  • A purified histidine-tagged Pte1p showed high activity toward short and medium chain length acyl-CoAs, including butyryl-CoA, decanoyl-CoA and 8-methyl-nonanoyl-CoA [2].
  • Lauroyl-CoA (C12) was about half as effective as palmitoyl-CoA, and decanoyl-CoA (C10) and butyl-CoA (C4) were inactive [3].
  • E. coli strains having a large deletion within the genomic tesB gene grew normally but retained a low level of thioesterase activity toward decanoyl-CoA [1].
  • We have now analysed the complete beta-oxidation of 5-HD-CoA using specially synthesised (and purified) substrates and enzymes, as well as isolated rat liver and heart mitochondria, and compared it with the metabolism of the physiological substrate decanoyl-CoA [4].
  • Consistent with the kinetic data, 5-hydroxydecanoyl-CoA alone acted as a weak substrate in isolated mitochondria, whereas addition of 100 mum 5-HD-CoA inhibited the metabolism of decanoyl-CoA or lauryl-carnitine [4].

Biological context of Decanoyl-coenzyme A


Anatomical context of Decanoyl-coenzyme A


Gene context of Decanoyl-coenzyme A

  • We found the recombinant beta-cell K(ATP) channel (SUR1/Kir6.2) to be much less sensitive to medium-chain acyl CoAs (decanoyl CoA: 124% +/- 15% v 231% +/- 25% in SUR2A/Kir6.2), suggesting a role for the cardiac sulfonylurea receptor, SUR2A, in the molecular mechanism of activation by these compounds [8].
  • These results suggest that MCAD-deficient cells readily convert decanoyl-CoA into octanoyl-CoA [9].

Analytical, diagnostic and therapeutic context of Decanoyl-coenzyme A


  1. Cloning, sequencing, and characterization of Escherichia coli thioesterase II. Naggert, J., Narasimhan, M.L., DeVeaux, L., Cho, H., Randhawa, Z.I., Cronan, J.E., Green, B.N., Smith, S. J. Biol. Chem. (1991) [Pubmed]
  2. The Peroxisomal Acyl-CoA Thioesterase Pte1p from Saccharomyces cerevisiae Is Required for Efficient Degradation of Short Straight Chain and Branched Chain Fatty Acids. Maeda, I., Delessert, S., Hasegawa, S., Seto, Y., Zuber, S., Poirier, Y. J. Biol. Chem. (2006) [Pubmed]
  3. Regulation of asialoglycoprotein receptor activity by a novel inactivation/reactivation cycle. Receptor reactivation in permeable rat hepatocytes is mediated by fatty acyl coenzyme A. Weigel, P.H., Oka, J.A. J. Biol. Chem. (1993) [Pubmed]
  4. 5-Hydroxydecanoate is metabolised in mitochondria and creates a rate-limiting bottleneck for beta-oxidation of fatty acids. Hanley, P.J., Dröse, S., Brandt, U., Lareau, R.A., Banerjee, A.L., Srivastava, D.K., Banaszak, L.J., Barycki, J.J., Van Veldhoven, P.P., Daut, J. J. Physiol. (Lond.) (2005) [Pubmed]
  5. Evidence of two catalytically active carnitine medium/long chain acyltransferases in rat liver peroxisomes. Singh, H., Beckman, K., Poulos, A. J. Lipid Res. (1996) [Pubmed]
  6. A study of the distribution of acyl-CoA hydrolases and acyl-L-carnitine hydrolases in guinea-pig small intestine. Andersen, K.J., Berge, R.K. Comparative biochemistry and physiology. A, Comparative physiology. (1982) [Pubmed]
  7. Accumulation of medium chain acyl-CoAs during beta-oxidation of long chain fatty acid by isolated peroxisomes from rat liver. Hashimoto, F., Furuya, Y., Hayashi, H. Biol. Pharm. Bull. (2001) [Pubmed]
  8. Acyl coenzyme A esters differentially activate cardiac and beta-cell adenosine triphosphate-sensitive potassium channels in a side-chain length-specific manner. Fox, J.E., Magga, J., Giles, W.R., Light, P.E. Metab. Clin. Exp. (2003) [Pubmed]
  9. Investigation of beta-oxidation intermediates in normal and MCAD-deficient human fibroblasts using tandem mass spectrometry. Nada, M.A., Chace, D.H., Sprecher, H., Roe, C.R. Biochem. Mol. Med. (1995) [Pubmed]
  10. Involvement of one of two enoyl-CoA hydratases and enoyl-CoA reductase in the acetyl-CoA-dependent elongation of medium chain fatty acids by Mycobacterium smegmatis. Shimakata, T., Fujita, Y., Kusaka, T. J. Biochem. (1980) [Pubmed]
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