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Chemical Compound Review

aminate     methanoate

Synonyms: formate, formylate, carboxyl-group, Formate ion, MCFA anions, ...
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Disease relevance of methanoic acid

  • The two patients with ocular signs and acidosis had high serum formate concentrations (75 and 55 mg/dL, respectively) [1].
  • The special elongation factor SelB of Escherichia coli promotes selenocysteine incorporation into formate dehydrogenases [2].
  • The pH-dependent kinetics of this inactivator were consistent with the requirement of an unprotonated carboxyl group in the active site of the enzyme, suggesting that HIV-1 protease is also an aspartic protease [3].
  • Furthermore, the coupled electron transport chain from formate to nitrite of Wolinella succinogenes has been reconstituted by incorporating the purified enzymes into liposomes [4].
  • Formate dehydrogenase from Methylosinus trichosporium OB3b. Purification and spectroscopic characterization of the cofactors [5].

Psychiatry related information on methanoic acid

  • This bi-enzyme sensor has achieved a linear range of 1-300 microM and a detection limit of 1.98 x 10(-7) M for formate (S/N=3), with the response time of 4 min [6].

High impact information on methanoic acid

  • Chemical modification of the brain receptor provides evidence for the importance of a carboxyl group that interacts with ligands at the receptor binding site [7].
  • In phospholipid bilayers the carboxyl group of HA is localized in the aqueous interface, with an apparent pKa (7.4) similar to other fatty acids; the acyl chain must then penetrate very deeply into the membrane [8].
  • The measured apical membrane formic acid permeability is too small to support all of transcellular NaCl absorption in the rat by a mechanism that involves Na/H-Cl/formate transporters operating in parallel with formic acid nonionic diffusion [9].
  • The presence of a carboxyl group also appears to alter active ion transport, but this effect cannot be attributed to enhanced diffusion of acid into the tissue [10].
  • It is concluded that the presence of a sufficient concentration of an exposed carboxyl group on the mucosal side of the tissue causes an increase in the permeability of the mucosa to acid [10].

Chemical compound and disease context of methanoic acid


Biological context of methanoic acid


Anatomical context of methanoic acid


Associations of methanoic acid with other chemical compounds

  • Clues that connect this interstellar hot core chemistry to the solar system can be found in the cometary detection of methyl formate and the interferometric maps of cometary methanol [25].
  • In combination with mutagenesis results, a hydrogen-bonding network from the water molecule adjacent to the iron ligand to the protein surface of the distal pocket through the hydroxyl group of Ser 286 and the carboxyl group of Asp 393 can be assigned to a pathway for proton delivery during the NO reduction reaction [26].
  • The interaction of ICAMs with LFA-1 is known to be mediated by a divalent cation bound to the insertion (I)-domain on the alpha chain of LFA-1 and the carboxyl group of a conserved glutamic acid residue on ICAMs [27].
  • An in vivo ESR spin-trapping study: free radical generation in rats from formate intoxication--role of the Fenton reaction [28].
  • Upon inhibitor binding, the side chains of Tyr-241 and Tyr-300 turn, forming a hydrogen-bonding triad with the carboxyl group of the inhibitor's cysteine moiety, allowing this moiety to fit tightly into the cysteine-binding site with concomitant accommodation of its side chain into a shallow pocket [29].

Gene context of methanoic acid

  • The sequence contains three open reading frames of sizes appropriate to encode the three subunits of formate dehydrogenase-N. fdnG contains an in-frame UGA codon that specifies selenocysteine incorporation, and the predicted amino acid sequence of FdnG shows similarity to two other bacterial formate dehydrogenase enzymes [30].
  • Taken together these data demonstrate the importance of both Arg269 and Lys220 of RAR-beta for the binding of RA, possibly by interacting with the negatively charged carboxyl group of RA [31].
  • We conclude that mouse Slc26a6 has affinity for oxalate, sulfate, and HCO(3)(-) in addition to Cl(-) and formate and can function in multiple exchange modes involving pairs of these anions [32].
  • GRIP1 PDZ7 contains a closed carboxyl group-binding pocket and a narrow alphaB/betaB-groove that is not likely to bind to classical PDZ ligands [33].
  • Moreover, it could be shown that there was a corresponding reduction of approximately 50% in the amount of formate excreted by a focA mutant into the culture medium [34].

Analytical, diagnostic and therapeutic context of methanoic acid

  • As measured by miniature glass pH microelectrodes, this lack of formate effect on JV was related to a less extensive acidification of the tubule fluid when high HCO-3 solutions were used as perfusate [35].
  • Several apparent microscopic ionization constants have been determined from the carboxyl group NMR titration curves, and possible assignments are discussed [36].
  • Sequence analyses of tryptic, V8 protease-, and Asp-N protease-generated peptides show that the heme propionyl carboxyl group at the surface of the cytochrome forms an ester bond with Ser162 of the reductase, thus implicating Lys163 as the normal participant in ionic bonding between the active sites of the two proteins [37].
  • Noting that nisin has Ile at position 4, site-directed mutagenesis was used to change Glu4 of subtilin to Ile, in order to eliminate this carboxyl-group participation [38].
  • The transport characteristics of aminocephalosporin antibiotics, possessing an alpha-amino group and a carboxyl group, in brush-border membranes isolated from rabbit small intestine have been studied by a rapid filtration technique [39].


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  2. In vitro and in vivo characterization of novel mRNA motifs that bind special elongation factor SelB. Klug, S.J., Hüttenhofer, A., Kromayer, M., Famulok, M. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Human immunodeficiency virus 1 protease expressed in Escherichia coli behaves as a dimeric aspartic protease. Meek, T.D., Dayton, B.D., Metcalf, B.W., Dreyer, G.B., Strickler, J.E., Gorniak, J.G., Rosenberg, M., Moore, M.L., Magaard, V.W., Debouck, C. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
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  9. Contributions of cellular leak pathways to net NaHCO3 and NaCl absorption. Preisig, P.A., Alpern, R.J. J. Clin. Invest. (1989) [Pubmed]
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  11. A radical-chemical route to acetyl-CoA: the anaerobically induced pyruvate formate-lyase system of Escherichia coli. Knappe, J., Sawers, G. FEMS Microbiol. Rev. (1990) [Pubmed]
  12. Escherichia coli formate-hydrogen lyase. Purification and properties of the selenium-dependent formate dehydrogenase component. Axley, M.J., Grahame, D.A., Stadtman, T.C. J. Biol. Chem. (1990) [Pubmed]
  13. Cloning, sequencing, and expression in escherichia coli of OxlT, the oxalate:formate exchange protein of Oxalobacter formigenes. Abe, K., Ruan, Z.S., Maloney, P.C. J. Biol. Chem. (1996) [Pubmed]
  14. Characterization of the menaquinone reduction site in the diheme cytochrome b membrane anchor of Wolinella succinogenes NiFe-hydrogenase. Gross, R., Pisa, R., Sänger, M., Lancaster, C.R., Simon, J. J. Biol. Chem. (2004) [Pubmed]
  15. The interaction of carboxyl group reagents with the Rhodospirillum rubrum F1-ATPase and its isolated beta-subunit. Khananshvili, D., Gromet-Elhanan, Z. J. Biol. Chem. (1983) [Pubmed]
  16. Characterization of the iron- and 2-oxoglutarate-binding sites of human prolyl 4-hydroxylase. Myllyharju, J., Kivirikko, K.I. EMBO J. (1997) [Pubmed]
  17. The Chlamydomonas reinhardtii Nar1 gene encodes a chloroplast membrane protein involved in nitrite transport. Rexach, J., Fernández, E., Galván, A. Plant Cell (2000) [Pubmed]
  18. The genome sequence of the anaerobic, sulfate-reducing bacterium Desulfovibrio vulgaris Hildenborough. Heidelberg, J.F., Seshadri, R., Haveman, S.A., Hemme, C.L., Paulsen, I.T., Kolonay, J.F., Eisen, J.A., Ward, N., Methe, B., Brinkac, L.M., Daugherty, S.C., Deboy, R.T., Dodson, R.J., Durkin, A.S., Madupu, R., Nelson, W.C., Sullivan, S.A., Fouts, D., Haft, D.H., Selengut, J., Peterson, J.D., Davidsen, T.M., Zafar, N., Zhou, L., Radune, D., Dimitrov, G., Hance, M., Tran, K., Khouri, H., Gill, J., Utterback, T.R., Feldblyum, T.V., Wall, J.D., Voordouw, G., Fraser, C.M. Nat. Biotechnol. (2004) [Pubmed]
  19. Inhibition of human platelet phospholipase A2 activity by unsaturated fatty acids. Ballou, L.R., Cheung, W.Y. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  20. Chicken neutrophils: oxidative metabolism in phagocytic cells devoid of myeloperoxidase. Penniall, R., Spitznagel, J.K. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  21. Chloride/formate exchange with formic acid recycling: a mechanism of active chloride transport across epithelial membranes. Karniski, L.P., Aronson, P.S. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  22. Conversion of isoaspartyl peptides to normal peptides: implications for the cellular repair of damaged proteins. McFadden, P.N., Clarke, S. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  23. Structure of sortase, the transpeptidase that anchors proteins to the cell wall of Staphylococcus aureus. Ilangovan, U., Ton-That, H., Iwahara, J., Schneewind, O., Clubb, R.T. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
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  25. Interferometric observations of large biologically interesting interstellar and cometary molecules. Snyder, L.E. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  26. Crystal structure of nitric oxide reductase from denitrifying fungus Fusarium oxysporum. Park, S.Y., Shimizu, H., Adachi, S., Nakagawa, A., Tanaka, I., Nakahara, K., Shoun, H., Obayashi, E., Nakamura, H., Iizuka, T., Shiro, Y. Nat. Struct. Biol. (1997) [Pubmed]
  27. The structure of the two amino-terminal domains of human ICAM-1 suggests how it functions as a rhinovirus receptor and as an LFA-1 integrin ligand. Bella, J., Kolatkar, P.R., Marlor, C.W., Greve, J.M., Rossmann, M.G. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  28. An in vivo ESR spin-trapping study: free radical generation in rats from formate intoxication--role of the Fenton reaction. Dikalova, A.E., Kadiiska, M.B., Mason, R.P. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  29. Crystal structure of gamma-glutamylcysteine synthetase: insights into the mechanism of catalysis by a key enzyme for glutathione homeostasis. Hibi, T., Nii, H., Nakatsu, T., Kimura, A., Kato, H., Hiratake, J., Oda, J. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  30. Nitrate-inducible formate dehydrogenase in Escherichia coli K-12. I. Nucleotide sequence of the fdnGHI operon and evidence that opal (UGA) encodes selenocysteine. Berg, B.L., Li, J., Heider, J., Stewart, V. J. Biol. Chem. (1991) [Pubmed]
  31. Arg269 and Lys220 of retinoic acid receptor-beta are important for the binding of retinoic acid. Tairis, N., Gabriel, J.L., Gyda, M., Soprano, K.J., Soprano, D.R. J. Biol. Chem. (1994) [Pubmed]
  32. Specificity of anion exchange mediated by mouse Slc26a6. Jiang, Z., Grichtchenko, I.I., Boron, W.F., Aronson, P.S. J. Biol. Chem. (2002) [Pubmed]
  33. PDZ7 of glutamate receptor interacting protein binds to its target via a novel hydrophobic surface area. Feng, W., Fan, J.S., Jiang, M., Shi, Y.W., Zhang, M. J. Biol. Chem. (2002) [Pubmed]
  34. Isolation and characterization of hypophosphite--resistant mutants of Escherichia coli: identification of the FocA protein, encoded by the pfl operon, as a putative formate transporter. Suppmann, B., Sawers, G. Mol. Microbiol. (1994) [Pubmed]
  35. Effect of formate on volume reabsorption in the rabbit proximal tubule. Schild, L., Giebisch, G., Karniski, L.P., Aronson, P.S. J. Clin. Invest. (1987) [Pubmed]
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  37. Characterization of the covalent cross-links of the active sites of amidinated cytochrome b5 and NADH:cytochrome b5 reductase. Strittmatter, P., Hackett, C.S., Korza, G., Ozols, J. J. Biol. Chem. (1990) [Pubmed]
  38. Enhancement of the chemical and antimicrobial properties of subtilin by site-directed mutagenesis. Liu, W., Hansen, J.N. J. Biol. Chem. (1992) [Pubmed]
  39. H+ coupled uphill transport of aminocephalosporins via the dipeptide transport system in rabbit intestinal brush-border membranes. Okano, T., Inui, K., Maegawa, H., Takano, M., Hori, R. J. Biol. Chem. (1986) [Pubmed]
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