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Chemical Compound Review

N-FORMYLMETHIONINE     (2S)-2-formamido-4- methylsulfanyl-butanoate

Synonyms: CHEBI:57809, AC1NRB2E, ZINC01529464, N-formyl-L-methioninate, N-formyl-L-methioninate(1-), ...
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Disease relevance of N-formyl-L-methionine

 

High impact information on N-formyl-L-methionine

  • Bacteria similarly initiate protein synthesis with N-formylmethionine; indeed, we established that Hmt can also present prokaryotic peptides in an N-formyl-dependent manner [3].
  • Like bacteria, mitochondria initiate protein synthesis with an N-formylmethionine residue [4].
  • Elongation factor P (EFP) is a protein that stimulates the peptidyltransferase activity of fully assembled 70 S prokaryotic ribosomes and enhances the synthesis of certain dipeptides initiated by N-formylmethionine [5].
  • Cross-recognition of N-formylmethionine peptides is a general characteristic of H2-M3-restricted CD8+ T cells [6].
  • Peptide deformylase (PDF) is an essential bacterial metalloenzyme which deformylates the N-formylmethionine of newly synthesized polypeptides and as such represents a novel target for antibacterial chemotherapy [7].
 

Biological context of N-formyl-L-methionine

 

Anatomical context of N-formyl-L-methionine

  • Leucocyte or platelet N-formylmethionine deformylase may be important in modulation of neutrophil responses to chemoattractant formylmethionyl peptides or similar compounds [11].
  • H2-M3-restricted CD8+ T cells can exhibit cross-reactivity to different bacterially derived N-formylmethionine peptides [6].
  • Addition of TD beta gamma isolated from TD prepared with GTP[S] (TD beta gamma GTP[S]) to HL 60 membranes abolished high-affinity binding of fMet-Leu-[3H]Phe (fMet, N-formylmethionine) to its receptor [12].
  • Membranes of myeloid differentiated human leukemia (HL 60) cells contain receptors for the chemotactic peptide, fMet-Leu-Phe (fMet, N-formylmethionine), interacting with pertussis-toxin-sensitive guanine-nucleotide-binding proteins (G proteins) [13].
 

Associations of N-formyl-L-methionine with other chemical compounds

 

Gene context of N-formyl-L-methionine

 

Analytical, diagnostic and therapeutic context of N-formyl-L-methionine

  • A specific enzyme for the liberation of N-terminal N-formylmethionine from N-formylmethionyl peptides was purified 4750-fold from rat liver by successive applications of (NH4)SO4 precipitation, DEAE-cellulose, N-formylbestatin-AH-Sepharose 4B and AH-Sepharose 4B chromatography followed by Sepharose CL-6B gel filtration [19].

References

  1. Translation of poliovirus RNA in vitro: studies on n-formylmethionine-labeled polypeptides initiated in cell-free extracts prepared from poliovirus infected HeLa cells. Knauert, F., Ehrenfeld, E. Virology (1979) [Pubmed]
  2. Ribonucleases from the extreme thermophilic archaebacterium S. solfataricus. Fusi, P., Tedeschi, G., Aliverti, A., Ronchi, S., Tortora, P., Guerritore, A. Eur. J. Biochem. (1993) [Pubmed]
  3. Specialized functions of major histocompatibility complex class I molecules. II. Hmt binds N-formylated peptides of mitochondrial and prokaryotic origin. Shawar, S.M., Vyas, J.M., Rodgers, J.R., Cook, R.G., Rich, R.R. J. Exp. Med. (1991) [Pubmed]
  4. Mitochondrial N-formylmethionyl proteins as chemoattractants for neutrophils. Carp, H. J. Exp. Med. (1982) [Pubmed]
  5. The gene encoding the elongation factor P protein is essential for viability and is required for protein synthesis. Aoki, H., Dekany, K., Adams, S.L., Ganoza, M.C. J. Biol. Chem. (1997) [Pubmed]
  6. Cross-recognition of N-formylmethionine peptides is a general characteristic of H2-M3-restricted CD8+ T cells. Ploss, A., Tran, A., Menet, E., Leiner, I., Pamer, E.G. Infect. Immun. (2005) [Pubmed]
  7. Antibiotic activity and characterization of BB-3497, a novel peptide deformylase inhibitor. Clements, J.M., Beckett, R.P., Brown, A., Catlin, G., Lobell, M., Palan, S., Thomas, W., Whittaker, M., Wood, S., Salama, S., Baker, P.J., Rodgers, H.F., Barynin, V., Rice, D.W., Hunter, M.G. Antimicrob. Agents Chemother. (2001) [Pubmed]
  8. Inhibition of the release factor-dependent termination reaction on ribosomes by DnaJ and the N-terminal peptide of rhodanese. Kudlicki, W., Odom, O.W., Merrill, G., Kramer, G., Hardesty, B. J. Bacteriol. (1995) [Pubmed]
  9. Purification and sequencing of cytochrome b from potato reveals methionine cleavage of a mitochondrially encoded protein. Braun, H.P., Schmitz, U.K. FEBS Lett. (1993) [Pubmed]
  10. Methylprednisolone reduces airway microvascular permeability but not airway resistance induced by N-formylmethionine leucyl-phenylalanine in the rabbit. Matheson, M., McClean, M., Rynell, A.C., Berend, N. Respirology (2004) [Pubmed]
  11. N-formyl-L-methionine deformylase activity in human leucocytes and platelets. Ackerman, S.K., Douglas, S.D. Biochem. J. (1979) [Pubmed]
  12. Activation of signal-transducing guanine-nucleotide-binding regulatory proteins by guanosine 5'-[gamma-thio]triphosphate. Information transfer by intermediately thiophosphorylated beta gamma subunits. Wieland, T., Ulibarri, I., Gierschik, P., Jakobs, K.H. Eur. J. Biochem. (1991) [Pubmed]
  13. Role of GDP in formyl-peptide-receptor-induced activation of guanine-nucleotide-binding proteins in membranes of HL 60 cells. Wieland, T., Kreiss, J., Gierschik, P., Jakobs, K.H. Eur. J. Biochem. (1992) [Pubmed]
  14. Functional modification by cholera-toxin-catalyzed ADP-ribosylation of a guanine-nucleotide-binding regulatory protein serving as the substrate of pertussis toxin. Iiri, T., Ohoka, Y., Ui, M., Katada, T. Eur. J. Biochem. (1991) [Pubmed]
  15. Neutrophil beta-adrenergic receptor responses are potentiated by acute exposure to phorbol ester without changes in receptor distribution or coupling. Kilfeather, S.A., Stein, M., O'Malley, K. Life Sci. (1991) [Pubmed]
  16. In vitro synthesis of the respiratory NADH dehydrogenase of Escherichia coli. Role of UUG as initiation codon. Poulis, M.I., Shaw, D.C., Campbell, H.D., Young, I.G. Biochemistry (1981) [Pubmed]
  17. Increased peptide deformylase activity for N-formylmethionine processing of proteins overexpressed in Escherichia coli: application to homogeneous rubredoxin production. Tang, J., Hernández, G., LeMaster, D.M. Protein Expr. Purif. (2004) [Pubmed]
  18. Novel approaches to antimicrobial therapy: peptide deformylase. Waller, A.S., Clements, J.M. Current opinion in drug discovery & development. (2002) [Pubmed]
  19. Purification and properties of N-formylmethionine aminopeptidase from rat liver. Suda, H., Yamamoto, K., Aoyagi, T., Umezawa, H. Biochim. Biophys. Acta (1980) [Pubmed]
 
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