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Chemical Compound Review

AG-E-89516     2-[[4-[(2-amino-4-oxo- 5,6,7,8-tetrahydro...

Synonyms: AC1Q5SFA, CTK4G0609, AR-1J8787, AC1L189V, 10-CHO-THF, ...
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Disease relevance of C00234


High impact information on C00234


Biological context of C00234


Anatomical context of C00234


Associations of C00234 with other chemical compounds


Gene context of C00234

  • We have studied yeast mutants carrying chromosomal disruptions of the genes encoding the mitochondrial C(1)-tetrahydrofolate (C(1)-THF) synthase (MIS1), necessary for synthesis of 10-formyl-THF, and the methionyl-tRNA formyltransferase (open reading frame YBL013W; designated FMT1) [19].
  • In eucaryotes, 10-formyltetrahydrofolate (formyl-THF) synthetase, 5,10-methenyl-THF cyclohydrolase, and NADP(+)-dependent 5,10-methylene-THF dehydrogenase activities are present on a single polypeptide termed C1-THF synthase [20].
  • The amino-terminal domain of FDH shares some sequence identity with several other enzymes utilizing 10-formyl-THF as a substrate [21].
  • Disruption of the mthfd1 gene reveals a monofunctional 10-formyltetrahydrofolate synthetase in mammalian mitochondria [22].
  • These results suggest that unlike the trifunctional form of C1-tetrahydrofolate synthase in the other eukaryotes examined, 10-formyltetrahydrofolate synthetase in spinach leaves is monofunctional and 5,10-methyl-enetetrahydrofolate dehydrogenase and 5,10-methenyltetrahydrofolate cyclohydrolase appear to be bifunctional [23].

Analytical, diagnostic and therapeutic context of C00234


  1. Identification of a heritable deficiency of the folate-dependent enzyme 10-formyltetrahydrofolate dehydrogenase in mice. Champion, K.M., Cook, R.J., Tollaksen, S.L., Giometti, C.S. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  2. A complex of N5,N10-methylenetetrahydrofolate dehydrogenase and N5,N10-methenyltetrahydrofolate cyclohydrolase in Escherichia coli. Purification, subunit structure, and allosteric inhibition by N10-formyltetrahydrofolate. Dev, I.K., Harvey, R.J. J. Biol. Chem. (1978) [Pubmed]
  3. Sequence and expression of the gene for N10-formyltetrahydrofolate synthetase from Clostridium cylindrosporum. Rankin, C.A., Haslam, G.C., Himes, R.H. Protein Sci. (1993) [Pubmed]
  4. The hydrogenase gene cluster of Rhizobium leguminosarum bv. viciae contains an additional gene (hypX), which encodes a protein with sequence similarity to the N10-formyltetrahydrofolate-dependent enzyme family and is required for nickel-dependent hydrogenase processing and activity. Rey, L., Fernández, D., Brito, B., Hernando, Y., Palacios, J.M., Imperial, J., Ruiz-Argüeso, T. Mol. Gen. Genet. (1996) [Pubmed]
  5. Immunological crossreactivity of eukaryotic C1-tetrahydrofolate synthase and prokaryotic 10-formyltetrahydrofolate synthetase. Staben, C., Rabinowitz, J.C. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  6. Mitochondrial NAD-dependent methylenetetrahydrofolate dehydrogenase-methenyltetrahydrofolate cyclohydrolase is essential for embryonic development. Di Pietro, E., Sirois, J., Tremblay, M.L., MacKenzie, R.E. Mol. Cell. Biol. (2002) [Pubmed]
  7. Characterization of mammalian phosphoribosylglycineamide formyltransferase from transformed cells. Daubner, S.C., Benkovic, S.J. Cancer Res. (1985) [Pubmed]
  8. C1-Tetrahydrofolate synthase from rabbit liver. Structural and kinetic properties of the enzyme and its two domains. Villar, E., Schuster, B., Peterson, D., Schirch, V. J. Biol. Chem. (1985) [Pubmed]
  9. Serine hydroxymethyltransferase catalyzes the hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate. Stover, P., Schirch, V. J. Biol. Chem. (1990) [Pubmed]
  10. Isolation and characterization of the Saccharomyces cerevisiae MIS1 gene encoding mitochondrial C1-tetrahydrofolate synthase. Shannon, K.W., Rabinowitz, J.C. J. Biol. Chem. (1988) [Pubmed]
  11. Nucleotide sequence of the Clostridium acidiurici ("Clostridium acidi-urici") gene for 10-formyltetrahydrofolate synthetase shows extensive amino acid homology with the trifunctional enzyme C1-tetrahydrofolate synthase from Saccharomyces cerevisiae. Whitehead, T.R., Rabinowitz, J.C. J. Bacteriol. (1988) [Pubmed]
  12. Compartmentation of folate metabolism in rat pancreas: nitrous oxide inactivation of methionine synthase leads to accumulation of 5-methyltetrahydrofolate in cytosol. Horne, D.W., Holloway, R.S. J. Nutr. (1997) [Pubmed]
  13. Crystallization and preliminary X-ray diffraction analysis of recombinant hydrolase domain of 10-formyltetrahydrofolate dehydrogenase. Chumanevich, A.A., Davies, C., Krupenko, S.A. Acta Crystallogr. D Biol. Crystallogr. (2002) [Pubmed]
  14. Metabolism of 10-formyldihydrofolate in humans. Baggott, J.E., Tamura, T. Biomed. Pharmacother. (2001) [Pubmed]
  15. Resolution of rat liver 10-formyltetrahydrofolate dehydrogenase/hydrolase activities. Case, G.L., Kaisaki, P.J., Steele, R.D. J. Biol. Chem. (1988) [Pubmed]
  16. Identification and biochemical properties of 10-formyldihydrofolate, a novel folate found in methotrexate-treated cells. Baram, J., Chabner, B.A., Drake, J.C., Fitzhugh, A.L., Sholar, P.W., Allegra, C.J. J. Biol. Chem. (1988) [Pubmed]
  17. Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria. Brookes, P.S., Baggott, J.E. Biochemistry (2002) [Pubmed]
  18. Inhibitory effects of histidine and their reversal. The roles of pyruvate carboxylase and N10-formyltetrahydrofolate dehydrogenase. Scrutton, M.C., Beis, I. Biochem. J. (1979) [Pubmed]
  19. Initiation of protein synthesis in Saccharomyces cerevisiae mitochondria without formylation of the initiator tRNA. Li, Y., Holmes, W.B., Appling, D.R., RajBhandary, U.L. J. Bacteriol. (2000) [Pubmed]
  20. Molecular genetic analysis of Saccharomyces cerevisiae C1-tetrahydrofolate synthase mutants reveals a noncatalytic function of the ADE3 gene product and an additional folate-dependent enzyme. Barlowe, C.K., Appling, D.R. Mol. Cell. Biol. (1990) [Pubmed]
  21. On the role of conserved histidine 106 in 10-formyltetrahydrofolate dehydrogenase catalysis: connection between hydrolase and dehydrogenase mechanisms. Krupenko, S.A., Vlasov, A.P., Wagner, C. J. Biol. Chem. (2001) [Pubmed]
  22. Disruption of the mthfd1 gene reveals a monofunctional 10-formyltetrahydrofolate synthetase in mammalian mitochondria. Christensen, K.E., Patel, H., Kuzmanov, U., Mejia, N.R., MacKenzie, R.E. J. Biol. Chem. (2005) [Pubmed]
  23. Isolation, characterization, and structural organization of 10-formyltetrahydrofolate synthetase from spinach leaves. Nour, J.M., Rabinowitz, J.C. J. Biol. Chem. (1991) [Pubmed]
  24. Purification, crystallization, and preliminary X-ray studies of 10-formyltetrahydrofolate synthetase from Clostridia acidici-urici. D'Ari, L., Cheung, E., Rabinowitz, J.C., Bolduc, J.M., Huang, J.Y., Stoddard, B.L. Proteins (1997) [Pubmed]
  25. Site-directed mutagenesis of a highly conserved aspartate in the putative 10-formyl-tetrahydrofolate binding site of yeast C1-tetrahydrofolate synthase. Kirksey, T.J., Appling, D.R. Arch. Biochem. Biophys. (1996) [Pubmed]
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