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Chemical Compound Review

imidates     methanamide

Synonyms: formamid, formamide, Methanamid, Methanamide, carboxamides, ...
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Disease relevance of methanamide

  • The messenger RNAs encoding two late adenovirus serotype 2 (Ad2) proteins, fiber and 100K, were purified by hybridization to restriction endonuclease fragments of Ad2 DNA followed by electrophoresis on polyacrylamide gels containing 98% formamide [1].
  • The N-substituted formamide-degrading microorganism was identified as Arthrobacter pascens [2].
  • Superhelical covalently closed circular replicative form DNA (RF I) of coliphage M13 appears as a relaxed molecule that has a base-unpaired region in the form of a bubble (100 to 200 base pairs long) seen in electron micrographs when spread in the presence of formaldehyde and formamide or after pretreatment with glyoxal [3].
  • In this study, we found that a novel small molecule, functionally selective CCR5 agonist, 2,2-dichloro-1-(triphenylphosphonio)vinyl formamide perchlorate (YM-370749), down-modulates CCR5 from the cell surface without inducing a chemotactic response and inhibits HIV-1 replication [4].
  • Antigenomic Hepatitis delta virus ribozymes self-cleave in 18 M formamide [5].

High impact information on methanamide

  • By using a variety of protocols involving the dissociating agents sodium desoxycholate and formamide, as much cytosolic NF-kappa B can be found in the fraction from unstimulated 70Z/3 pre-B cells as is found in the nuclear extract from phorbol ester-activated cells [6].
  • RNA isolated from L cell mitochondria was hybridized to 32P-labeled, cloned L cell mitochondrial DNA restriction fragments in 70% formamide under conditions 5 degrees C above the melting temperature of the DNA-DNA duplex, but approximately 15 degrees C below the melting temperature of the RNA-DNA duplex [7].
  • Efficient self-cleavage in 10 M formamide or 5 M urea, also a property of the genomic sequence, was dependent on base-pairing in both stems [8].
  • Through hybridization at different formamide concentrations, the present study identifies one additional, highly conserved region at map positions 14-15 on the Ad2 genome [9].
  • The mechanical activity of frog sartorius muscle fibers can be uncoupled from the electrical activity of their surface membranes by immersing the preparation in Ringer solution containing either 1.5 or 2.0 M of formamide for 15--20 min [10].

Chemical compound and disease context of methanamide


Biological context of methanamide

  • The results illustrate how the enzyme and nearby H2O molecules stabilize the ionic intermediates in peptide hydrolysis, such that the reaction is calculated to have a barrier that is significantly smaller than the calculated and experimental base-catalyzed barrier of formamide hydrolysis in aqueous solution [16].
  • A formamide molecule was modeled into the system to mimic the function of active site residue Asn-105 [17].
  • Photocatalysis and the origin of life: synthesis of nucleoside bases from formamide on TiO2(001) single surfaces [18].
  • The incorporation of bacteriochlorophylls with attached small formamide polymers and the subsequent dimerization of these pigments in the lipid phase provide a model for studying the synergetic organization of polypeptides and bacteriochlorophyll clusters in the photosynthetic membrane [19].
  • Dimethyl sulfoxide and dimethyl formamide induced tolerance without cytotoxicity, but the kinetics of doing so was different from that seen with the other solvents [20].

Anatomical context of methanamide

  • Formamide does not affect the electrical activity of the sciatic nerve branch, and both endplate potentials and miniature endplate potentials may be recorded from the uncoupled muscles [10].
  • The globin mRNAs of reticulocyte polyribosomes from patients with hematological disorders were estimated by scanning the stained formamide gels [21].
  • Formamide gel electrophoresis separates the mRNA fraction from reticulocyte polyribosomes of adult humans into two major RNA species with migratory rates identical to those of the alpha- and beta-globin mRNAs of the rabbit [21].
  • The 60-70S RNA aggregate or its 30-40S RNA subunits obtained by heat or formamide treatment possess the same ability to serve as template in X. laevis oocytes [22].
  • Motor nerve terminal sprouting in formamide-treated inactive amphibian skeletal muscle [23].

Associations of methanamide with other chemical compounds

  • Elution with 50 micro M [3H]estradiol in 10% (vol/vol) dimethyl formamide/0.5 M sodium thiocyanate gave 40% recovery of [3H]estradiol-estrophilin showing 14% of the specific radioactivity expected for the pure complex [24].
  • The bond between the protein and the DNA is stable in alkali, 4 M guanidine-hydrochloride, 3.86 M hydroxylamine (pH 4,23), and in 98% formamide [25].
  • The addition of bacteriochlorophylls and bacteriopheophytins to formamide/water, 3:1 (vol/vol), (or water) containing small spherical micelles of Triton X-100 leads to the reorganization of the detergent into micelles that consist of 5000-40,000 amphiphilic molecules [19].
  • The quantum mechanical region includes imidazole+ and acetate- as models for His-57+ and Asp-102-, two hydrogen bonds from two formamide molecules to the oxyanion MIP or TSD, and three hydrogen bonds to Asp-102 [26].
  • Fractionation of the RNA on formamide-containing sucrose gradients before translation indicates that the desmin messenger RNA is larger than the vimentin messenger RNA and contains an extensive noncoding segment [27].

Gene context of methanamide

  • SDP1 DNA-binding activity was restored by treating a protein fraction containing SDP1 and I-SDP1 with the dissociating agent formamide [28].
  • We show here that, while the HTZ1 gene encoding H2A.Z is not essential in budding yeast, its disruption results in slow growth and formamide sensitivity [29].
  • Those genes susceptible to giving rise to formamide-sensitive alleles include the structural gene for DNA ligase, CDC9, and the structural gene for arginine permease, CAN1 [30].
  • Dimethyl formamide (20%) increased the hNMT activity by 8.5-, 8.5-, 5.5- and 3.5-fold when pp60(src), MARCKS, M2, and cAMP-dependent protein kinase-derived peptide substrates were used, respectively [31].
  • Of these, 117 clones remained under high stringency hybridization conditions (65 degrees C, 50% formamide, 0.1 x SSC, 0.1% SDS) and were identified as FMO1 (95 clones) or FMO5 (22 clones) [32].

Analytical, diagnostic and therapeutic context of methanamide


  1. Two adenovirus mRNAs have a common 5' terminal leader sequence encoded at least 10 kb upstream from their main coding regions. Klessig, D.F. Cell (1977) [Pubmed]
  2. Amine-synthesizing enzyme N-substituted formamide deformylase: screening, purification, characterization, and gene cloning. Fukatsu, H., Hashimoto, Y., Goda, M., Higashibata, H., Kobayashi, M. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  3. Base-unpaired regions in supercoiled replicative form DNA of coliphage M13. Dasgupta, S., Allison, D.P., Snyder, C.E., Mitra, S. J. Biol. Chem. (1977) [Pubmed]
  4. Structural basis for the interaction of CCR5 with a small molecule, functionally selective CCR5 agonist. Saita, Y., Kodama, E., Orita, M., Kondo, M., Miyazaki, T., Sudo, K., Kajiwara, K., Matsuoka, M., Shimizu, Y. J. Immunol. (2006) [Pubmed]
  5. Antigenomic Hepatitis delta virus ribozymes self-cleave in 18 M formamide. Smith, J.B., Dinter-Gottlieb, G. Nucleic Acids Res. (1991) [Pubmed]
  6. Activation of DNA-binding activity in an apparently cytoplasmic precursor of the NF-kappa B transcription factor. Baeuerle, P.A., Baltimore, D. Cell (1988) [Pubmed]
  7. The transcription map of mouse mitochondrial DNA. Battey, J., Clayton, D.A. Cell (1978) [Pubmed]
  8. A pseudoknot-like structure required for efficient self-cleavage of hepatitis delta virus RNA. Perrotta, A.T., Been, M.D. Nature (1991) [Pubmed]
  9. Defective expression of mouse adenovirus Fl in human cells. Antoine, G., Aleström, P., Schilling, R., Pettersson, U., Winnacker, E.L. EMBO J. (1982) [Pubmed]
  10. A new method for excitation-contraction uncoupling in frog skeletal muscle. del Castillo, J., Escalona de Motta, G. J. Cell Biol. (1978) [Pubmed]
  11. Polyoma virus has three late mRNA's: one for each virion protein. Siddell, S.G., Smith, A.E. J. Virol. (1978) [Pubmed]
  12. Characterization of group H streptococcal temperate bacteriophage phi 227. Nugent, K.M., Cole, R.M. J. Virol. (1977) [Pubmed]
  13. Positive regulation of amidase synthesis in Pseudomonas aeruginosa. Farin, F., Clarke, P.H. J. Bacteriol. (1978) [Pubmed]
  14. Oxalate, formate, formamide, and methanol metabolism in Thiobacillus novellus. Chandra, T.S., Shethna, Y.I. J. Bacteriol. (1977) [Pubmed]
  15. A method for quantitative recovery of DNA from plate lysates of bacteriophage lambda-derived clones. Mitchell, A. Anal. Biochem. (1993) [Pubmed]
  16. The nature of enzyme catalysis in trypsin. Weiner, S.J., Seibel, G.L., Kollman, P.A. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  17. A theoretical examination of the factors controlling the catalytic efficiency of the DNA-(adenine-N6)-methyltransferase from Thermus aquaticus. Newby, Z.E., Lau, E.Y., Bruice, T.C. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  18. Photocatalysis and the origin of life: synthesis of nucleoside bases from formamide on TiO2(001) single surfaces. Senanayake, S.D., Idriss, H. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  19. Distribution and self-organization of photosynthetic pigments in micelles: implication for the assembly of light-harvesting complexes and reaction centers in the photosynthetic membrane. Scherz, A., Rosenbach-Belkin, V., Fisher, J.R. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  20. Mechanistic implications of the induction of thermotolerance in Chinese hamster cells by organic solvents. Hahn, G.M., Shiu, E.C., West, B., Goldstein, L., Li, G.C. Cancer Res. (1985) [Pubmed]
  21. Further evidence of a quantitative deficiency of chain-specific globin mRNA in the thalassemia syndromes. Kazazian, H.H., Ginder, G.D., Snyder, P.G., Van Beneden, R.J., Woodhead, A.P. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  22. Frog oocytes synthesize and completely process the precursor polypeptide to virion structural proteins after microinjection of avian myeloblastosis virus RNA. Ghysdael, J., Hubert, E., Trávnícek, M., Bolognesi, D.P., Burny, A., Cleuter, Y., Huez, G., Kettmann, R., Marbaix, G., Portetelle, D., Chantrenne, H. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  23. Motor nerve terminal sprouting in formamide-treated inactive amphibian skeletal muscle. Wines, M.M., Letinsky, M.S. J. Neurosci. (1988) [Pubmed]
  24. Monoclonal antibodies to human estrogen receptor. Greene, G.L., Nolan, C., Engler, J.P., Jensen, E.V. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  25. Structure of a nicked DNA-protein complex isolated from simian virus 40: covalent attachment of the protein to DNA and nick specificity. Kasamatsu, H., Wu, M. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  26. Charge state of His-57-Asp-102 couple in a transition state analogue-trypsin complex: a molecular orbital study. Umeyama, H., Hirono, S., Nakagawa, S. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  27. In vitro translation of the intermediate filament proteins desmin and vimentin. O'Connor, C.M., Asai, D.J., Flytzanis, C.N., Lazarides, E. Mol. Cell. Biol. (1981) [Pubmed]
  28. In vitro regulation of a SIN3-dependent DNA-binding activity by stimulatory and inhibitory factors. Wang, H., Stillman, D.J. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  29. Histone H2A.Z has a conserved function that is distinct from that of the major H2A sequence variants. Jackson, J.D., Gorovsky, M.A. Nucleic Acids Res. (2000) [Pubmed]
  30. Formamide sensitivity: a novel conditional phenotype in yeast. Aguilera, A. Genetics (1994) [Pubmed]
  31. Enhanced activity of human N-myristoyltransferase by dimethyl sulfoxide and related solvents in the presence of serine/threonine-containing peptide substrates. Pasha, M.K., Dimmock, J.R., Hollenberg, M.D., Sharma, R.K. Biochem. Pharmacol. (2002) [Pubmed]
  32. Cloning and sequencing of flavin-containing monooxygenases FMO3 and FMO4 from rabbit and characterization of FMO3. Burnett, V.L., Lawton, M.P., Philpot, R.M. J. Biol. Chem. (1994) [Pubmed]
  33. Improved PCR sequencing with formamide. Zhang, W., Reading, C., Deisseroth, A.B. Trends Genet. (1992) [Pubmed]
  34. Systematic punctuation of eukaryotic DNA by A+T-rich sequences. Moreau, J., Matyash-Smirniaguina, L., Scherrer, K. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  35. Blood flow in transplantable bladder tumors treated with hematoporphyrin derivative and light. Selman, S.H., Kreimer-Birnbaum, M., Klaunig, J.E., Goldblatt, P.J., Keck, R.W., Britton, S.L. Cancer Res. (1984) [Pubmed]
  36. Characterization of messenger RNA for fructose 1,6-bisphosphate aldolase A isozyme of rat ascites hepatoma AH 7974 cells. Sakiyama, S., Akiba, N., Fujimura, S. Cancer Res. (1979) [Pubmed]
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