N-Formylmethionine

N-Formylmethionine
Names
IUPAC name
N-Formylmethionine
Systematic IUPAC name
(S)-2-Formylamino-4-methylsulfanylbutanoic acid
Other names
2-Formylamino-4-methylsulfanyl-butyric acid; Formylmethionine; N-Formyl(methyl)homocysteine
Identifiers
3D model (JSmol)
Abbreviations fMet
ChEBI
ChemSpider
EC Number
  • 224-322-8
UNII
  • InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)
    Key: PYUSHNKNPOHWEZ-UHFFFAOYSA-N
  • CSCC[C@H](NC=O)C(O)=O
Properties
C6H11NO3S
Molar mass 177.22 g/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H319
P264+P265, P280, P305+P351+P338, P337+P317
Supplementary data page
N-Formylmethionine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Formylmethionine (fMet,[2] HCO-Met,[3] For-Met[3]) is a derivative of the amino acid methionine in which a formyl group has been added to the amino group. It is specifically used for initiation of protein synthesis from bacterial and organellar genes, and may be removed post-translationally.

fMet plays a crucial part in the protein synthesis of bacteria, mitochondria and chloroplasts. It is not used in cytosolic protein synthesis of eukaryotes, where eukaryotic nuclear genes are translated. It is also not used by Archaea. In the human body, fMet is recognized by the immune system as foreign material, or as an alarm signal released by damaged cells, and stimulates the body to fight against potential infection.

  1. ^ "N-Formyl-DL-methionine". pubchem.ncbi.nlm.nih.gov.
  2. ^ PubChem. "N-Formyl-DL-methionine". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-10-24.
  3. ^ a b Nomenclature and Symbolism for Amino Acids and Peptides, 3AA-18 and 3AA-19