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Chemical Compound Review

coenzyme A     [5-(6-aminopurin-9-yl)-4- hydroxy-2...

Synonyms: C4282_SIGMA, NSC-20274, NSC20274, AC1L18YY, S00343a, ...
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Disease relevance of coenzyme A

  • BACKGROUND: Acute fatty liver of pregnancy and the HELLP syndrome (hemolysis, elevated liver-enzyme levels, and a low platelet count) are serious hepatic disorders that may occur during pregnancy in women whose fetuses are later found to have a deficiency of long-chain 3-hydroxyacyl-coenzyme A (CoA) dehydrogenase [1].
  • The X-ray structure of a canonical GCN5-related N-acetyltransferase (GNAT), Serratia marcescens aminoglycoside 3-N-acetyltransferase, bound to coenzyme A (CoA) has been determined at 2.3 A resolution [2].
  • Alpha-methylacyl coenzyme A racemase as a marker for prostate cancer [3].
  • The effect of lovastatin (LOV), the inhibitor of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase, on linoleic acid (LA, 18:2n-6) metabolism was examined in human monocytic Mono Mac 6 (MM6) and hepatoma Hep G2 cells [4].
  • In the search for the mechanism by which hyperammonemia complicates propionic and methylmalonic acidemia the effects of a series of acyl-coenzyme A (CoA) derivatives were studied on the activity of N-acetylglutamate synthetase in rat liver mitochondria using acetyl-CoA as substrate [5].

Psychiatry related information on coenzyme A

  • A 5-month-old Korean boy who presented with lethargy and cardiomyopathy was diagnosed with very long chain acyl coenzyme A dehydrogenase (VLCAD) deficiency by organic acid, fatty acid, acylcarnitine, and molecular genetic analysis [6].
  • BACKGROUND: The beneficial effect of 3-hydroxy-3-methylglutyaryl co-enzyme A reductase inhibitors on cardiovascular risk reduction has been clearly established [7].
  • TG-lowering strategy in patients with HTG encompasses dietary modification and pharmacological agents, such as fibric acid derivatives, fish-oil and hydroxymethylglutaryl coenzyme A reductase inhibitors, which have, besides their known effects on the atherogenic lipid profile, beneficial effects on other determinants of cardiovascular disease [8].
  • We elaborated the rationale for decision making in 3-methylcrotonyl-coenzyme A (CoA) carboxylase deficiency (MCCD), which afflicts leucine catabolism, with reported outcomes ranging from asymptomatic to death [9].

High impact information on coenzyme A


Chemical compound and disease context of coenzyme A


Biological context of coenzyme A

  • Nucleotide sequence of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase, a glycoprotein of endoplasmic reticulum [18].
  • In addition to the synthetic potential of these cyclization catalysts, which is the main focus of this review, different enzymes for tailoring of peptide scaffolds as well as the manipulation of carrier proteins with reporter-labeled coenzyme A analogs are discussed [19].
  • OBJECTIVE: To estimate the frequency of fetal long-chain 3-hydroxyacyl coenzyme A dehydrogenase deficiency in pregnancies complicated by AFLP or HELLP syndrome [20].
  • The tGCN5/CoA/H3p19 structure reveals that a 12 amino acid core sequence mediates extensive contacts with the protein, providing the structural basis for substrate specificity by the GCN5/PCAF family of histone acetyltransferases [21].
  • Comparison with the tGCN5/CoA/H3p19Pi structure reveals that phospho-Ser10 and Thr11 mediate significant histone-protein interactions, and nucleate additional interactions distal to the phosphorylation site [21].

Anatomical context of coenzyme A


Associations of coenzyme A with other chemical compounds

  • Fatty acid oxidation and ketogenesis are stimulated simultaneously with a paradoxical stimulation of fatty acid synthesis, which may be linked by virtue of a blunted response of mitochondrial carnitine palmitoyltransferase I (CPT-I) to malonyl coenzyme A (CoA) [27].
  • In human cells, sterol is esterified to a storage form by acyl-coenzyme A (CoA): cholesterol acyl transferase (ACAT) [28].
  • To allow for the exchange of the second CoA-bound carboxyl group, we propose the deacylation of the once exchanged acid with spontaneous racemization (relative to the 13C-carboxyl group), followed by reacylation, thus exposing the labeled carboxyl to decarboxylation [29].
  • 0. High-performance liquid chromatography/mass spectrometry-determined enrichments in SMX-acetate attained stable plateau values, and hepatic acetyl-coenzyme A (CoA) dilution rate did not increase with refeeding (approximately 0.024 mmol/kg per min) [30].
  • The bifunctional enzyme carbon monoxide dehydrogenase/acetyl-coenzyme A (CoA) synthase (CODH/ACS) is a key enzyme in the Wood-Ljungdahl pathway of carbon fixation [31].

Gene context of coenzyme A


Analytical, diagnostic and therapeutic context of coenzyme A


  1. A fetal fatty-acid oxidation disorder as a cause of liver disease in pregnant women. Ibdah, J.A., Bennett, M.J., Rinaldo, P., Zhao, Y., Gibson, B., Sims, H.F., Strauss, A.W. N. Engl. J. Med. (1999) [Pubmed]
  2. Crystal structure of a GCN5-related N-acetyltransferase: Serratia marcescens aminoglycoside 3-N-acetyltransferase. Wolf, E., Vassilev, A., Makino, Y., Sali, A., Nakatani, Y., Burley, S.K. Cell (1998) [Pubmed]
  3. Alpha-methylacyl coenzyme A racemase as a marker for prostate cancer. Jiang, Z., Woda, B.A., Yang, X.J. JAMA (2002) [Pubmed]
  4. Lovastatin increases arachidonic acid levels and stimulates thromboxane synthesis in human liver and monocytic cell lines. Hrboticky, N., Tang, L., Zimmer, B., Lux, I., Weber, P.C. J. Clin. Invest. (1994) [Pubmed]
  5. Inhibition by propionyl-coenzyme A of N-acetylglutamate synthetase in rat liver mitochondria. A possible explanation for hyperammonemia in propionic and methylmalonic acidemia. Coude, F.X., Sweetman, L., Nyhan, W.L. J. Clin. Invest. (1979) [Pubmed]
  6. Very long chain acyl coenzyme A dehydrogenase deficiency in a 5-month-old Korean boy: identification of a novel mutation. Hahn, S.H., Lee, E.H., Jung, J.W., Hong, C.H., Yoon, H.R., Rinaldo, P., Sims, H., Gibson, B., Strauss, A.W. J. Pediatr. (1999) [Pubmed]
  7. Effect of garlic on lipid profile and psychopathologic parameters in people with mild to moderate hypercholesterolemia. Peleg, A., Hershcovici, T., Lipa, R., Anbar, R., Redler, M., Beigel, Y. Isr. Med. Assoc. J. (2003) [Pubmed]
  8. Hypertriglyceridemia: associated risks and effect of drug treatment. Jonkers, I.J., Smelt, A.H., van der Laarse, A. American journal of cardiovascular drugs : drugs, devices, and other interventions. (2001) [Pubmed]
  9. Newborn screening for 3-methylcrotonyl-CoA carboxylase deficiency: population heterogeneity of MCCA and MCCB mutations and impact on risk assessment. Stadler, S.C., Polanetz, R., Maier, E.M., Heidenreich, S.C., Niederer, B., Mayerhofer, P.U., Lagler, F., Koch, H.G., Santer, R., Fletcher, J.M., Ranieri, E., Das, A.M., Spiekerkötter, U., Schwab, K.O., Pötzsch, S., Marquardt, I., Hennermann, J.B., Knerr, I., Mercimek-Mahmutoglu, S., Kohlschmidt, N., Liebl, B., Fingerhut, R., Olgemöller, B., Muntau, A.C., Roscher, A.A., Röschinger, W. Hum. Mutat. (2006) [Pubmed]
  10. Stepwise assembly of functionally active transport vesicles. Ostermann, J., Orci, L., Tani, K., Amherdt, M., Ravazzola, M., Elazar, Z., Rothman, J.E. Cell (1993) [Pubmed]
  11. Control of the peroxisomal beta-oxidation pathway by a novel family of nuclear hormone receptors. Dreyer, C., Krey, G., Keller, H., Givel, F., Helftenbein, G., Wahli, W. Cell (1992) [Pubmed]
  12. Recurrent hypoglycemia associated with glutaric aciduria type II in an adult. Dusheiko, G., Kew, M.C., Joffe, B.I., Lewin, J.R., Mantagos, S., Tanaka, K. N. Engl. J. Med. (1979) [Pubmed]
  13. Solution structure of the catalytic domain of GCN5 histone acetyltransferase bound to coenzyme A. Lin, Y., Fletcher, C.M., Zhou, J., Allis, C.D., Wagner, G. Nature (1999) [Pubmed]
  14. Mutant holocarboxylase synthetase: evidence for the enzyme defect in early infantile biotin-responsive multiple carboxylase deficiency. Burri, B.J., Sweetman, L., Nyhan, W.L. J. Clin. Invest. (1981) [Pubmed]
  15. Subcellular localization of acetoacetate coenzyme A transferase in rat hepatomas. Fenselau, A., Wallis, K., Morris, H.P. Cancer Res. (1976) [Pubmed]
  16. Benzoic acid metabolism reflects hepatic mitochondrial function in rats with long-term extrahepatic cholestasis. Krähenbühl, L., Reichen, J., Talos, C., Krähenbühl, S. Hepatology (1997) [Pubmed]
  17. An autocrine factor from Reuber hepatoma cells that stimulates DNA synthesis and acetyl-CoA carboxylase. Characterization of biologic activity and evidence for a glycan structure. Witters, L.A., Watts, T.D. J. Biol. Chem. (1988) [Pubmed]
  18. Nucleotide sequence of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase, a glycoprotein of endoplasmic reticulum. Chin, D.J., Gil, G., Russell, D.W., Liscum, L., Luskey, K.L., Basu, S.K., Okayama, H., Berg, P., Goldstein, J.L., Brown, M.S. Nature (1984) [Pubmed]
  19. Chemoenzymatic and template-directed synthesis of bioactive macrocyclic peptides. Grünewald, J., Marahiel, M.A. Microbiol. Mol. Biol. Rev. (2006) [Pubmed]
  20. Prospective screening for pediatric mitochondrial trifunctional protein defects in pregnancies complicated by liver disease. Yang, Z., Yamada, J., Zhao, Y., Strauss, A.W., Ibdah, J.A. JAMA (2002) [Pubmed]
  21. Structural basis for histone and phosphohistone binding by the GCN5 histone acetyltransferase. Clements, A., Poux, A.N., Lo, W.S., Pillus, L., Berger, S.L., Marmorstein, R. Mol. Cell (2003) [Pubmed]
  22. Acetylcholine synthesis in synaptosomes: mode of transfer of mitochondrial acetyl coenzyme A. Benjamin, A.M., Quastel, J.H. Science (1981) [Pubmed]
  23. L-carnitine enhances excretion of propionyl coenzyme A as propionylcarnitine in propionic acidemia. Roe, C.R., Millington, D.S., Maltby, D.A., Bohan, T.P., Hoppel, C.L. J. Clin. Invest. (1984) [Pubmed]
  24. Genetic deficiency of short-chain acyl-coenzyme A dehydrogenase in cultured fibroblasts from a patient with muscle carnitine deficiency and severe skeletal muscle weakness. Coates, P.M., Hale, D.E., Finocchiaro, G., Tanaka, K., Winter, S.C. J. Clin. Invest. (1988) [Pubmed]
  25. Relationship between the coenzyme A and the carnitine pools in human skeletal muscle at rest and after exhaustive exercise under normoxic and acutely hypoxic conditions. Friolet, R., Hoppeler, H., Krähenbühl, S. J. Clin. Invest. (1994) [Pubmed]
  26. Cell migration in Drosophila. Forbes, A., Lehmann, R. Curr. Opin. Genet. Dev. (1999) [Pubmed]
  27. Plasma lipoproteins and regulation of hepatic metabolism of fatty acids in altered thyroid states. Heimberg, M., Olubadewo, J.O., Wilcox, H.G. Endocr. Rev. (1985) [Pubmed]
  28. Sterol esterification in yeast: a two-gene process. Yang, H., Bard, M., Bruner, D.A., Gleeson, A., Deckelbaum, R.J., Aljinovic, G., Pohl, T.M., Rothstein, R., Sturley, S.L. Science (1996) [Pubmed]
  29. Metabolism of methylmalonic acid in rats. Is methylmalonyl-coenzyme a racemase deficiency symptomatic in man? Montgomery, J.A., Mamer, O.A., Scriver, C.R. J. Clin. Invest. (1983) [Pubmed]
  30. Measurement of de novo hepatic lipogenesis in humans using stable isotopes. Hellerstein, M.K., Christiansen, M., Kaempfer, S., Kletke, C., Wu, K., Reid, J.S., Mulligan, K., Hellerstein, N.S., Shackleton, C.H. J. Clin. Invest. (1991) [Pubmed]
  31. Unraveling the structure and mechanism of acetyl-coenzyme A synthase. Hegg, E.L. Acc. Chem. Res. (2004) [Pubmed]
  32. Crystal structure of yeast Esa1 suggests a unified mechanism for catalysis and substrate binding by histone acetyltransferases. Yan, Y., Barlev, N.A., Haley, R.H., Berger, S.L., Marmorstein, R. Mol. Cell (2000) [Pubmed]
  33. Crystal structure of the histone acetyltransferase domain of the human PCAF transcriptional regulator bound to coenzyme A. Clements, A., Rojas, J.R., Trievel, R.C., Wang, L., Berger, S.L., Marmorstein, R. EMBO J. (1999) [Pubmed]
  34. The yeast mitochondrial carrier Leu5p and its human homologue Graves' disease protein are required for accumulation of coenzyme A in the matrix. Prohl, C., Pelzer, W., Diekert, K., Kmita, H., Bedekovics, T., Kispal, G., Lill, R. Mol. Cell. Biol. (2001) [Pubmed]
  35. The orphan nuclear receptor estrogen-related receptor alpha is a transcriptional regulator of the human medium-chain acyl coenzyme A dehydrogenase gene. Sladek, R., Bader, J.A., Giguère, V. Mol. Cell. Biol. (1997) [Pubmed]
  36. Polyunsaturated fatty acyl coenzyme A suppress the glucose-6-phosphatase promoter activity by modulating the DNA binding of hepatocyte nuclear factor 4 alpha. Rajas, F., Gautier, A., Bady, I., Montano, S., Mithieux, G. J. Biol. Chem. (2002) [Pubmed]
  37. Familial Hypercholesterolaemia Regression Study: a randomised trial of low-density-lipoprotein apheresis. Thompson, G.R., Maher, V.M., Matthews, S., Kitano, Y., Neuwirth, C., Shortt, M.B., Davies, G., Rees, A., Mir, A., Prescott, R.J. Lancet (1995) [Pubmed]
  38. Purification of 3-hydroxy-3-methylglutaryl-coenzyme A reductase from rat liver. Kleinsek, D.A., Ranganathan, S., Porter, J.W. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  39. Zonal heterogeneity of peroxisomal enzymes in rat liver: differential induction by three divergent hypolipidemic drugs. Lindauer, M., Beier, K., Völkl, A., Fahimi, H.D. Hepatology (1994) [Pubmed]
  40. Mucosal coenzyme A-dependent cholesterol esterification after intestinal perfusion of lipids in rats. Clark, S.B. J. Biol. Chem. (1979) [Pubmed]
  41. Improving health outcomes without increasing costs: maximizing the full potential of lipid reduction therapy in the primary and secondary prevention of coronary heart disease. Jacobson, T.A. Curr. Opin. Lipidol. (1997) [Pubmed]
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