Pyrrolysine

"Pyl" redirects here. For other uses, see Pyl (disambiguation).
Not to be confused with Pyrolysis.
Pyrrolysine
Names
IUPAC name
Pyrrolysine[1]
Systematic IUPAC name
N6-{[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]carbonyl}-L-lysine
Other names
(2S)-2-amino-6-{[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrole-2-carbonyl]-amino}-hexanoic acid
N6-(4-methyl-1,2-didehydropyrrolidine-5-carboxyl)-L-lysine
monomethylamine methyltransferase cofactor lysine adduct
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)/t8-,9+,10-/m1/s1 checkY
    Key: ZFOMKMMPBOQKMC-KXUCPTDWSA-N checkY
  • InChI=1/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)/t8-,9+,10-/m1/s1
    Key: ZFOMKMMPBOQKMC-KXUCPTDWBO
  • C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@@H](C(=O)O)N
  • Zwitterion: O=C(NCCCC[C@@H](C(=O)[O-])[NH3+])[C@@H]1/N=C\C[C@H]1C
Properties
C12H21N3O3
Molar mass 255.313 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pyrrolysine (symbol Pyl or O;[2] encoded by the 'amber' stop codon UAG) is an α-amino acid that is used in the biosynthesis of proteins in some methanogenic archaea and bacteria;[3][4] it is not present in humans. It contains an α-amino group (which is in the protonated –NH+
3 form under biological conditions) and a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions). Its pyrroline side-chain is similar to that of lysine in being basic and positively charged at neutral pH.[citation needed]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1392. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
  3. ^ Richard Cammack, ed. (2009). "Newsletter 2009". Biochemical Nomenclature Committee of IUPAC and NC-IUBMB. Pyrrolysine. Archived from the original on 2017-09-12. Retrieved 2012-04-16.
  4. ^ Rother, Michael; Krzycki, Joseph A. (2010-01-01). "Selenocysteine, Pyrrolysine, and the Unique Energy Metabolism of Methanogenic Archaea". Archaea. 2010: 1–14. doi:10.1155/2010/453642. ISSN 1472-3646. PMC 2933860. PMID 20847933.