Pyrrolysine

Pyrrolysine (symbol Pyl or O; 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; it is not present in humans. It contains an α-amino group (which is in the protonated –NH+
3 form under biological conditions), 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.

"Pyl" redirects here. For other uses, see Pyl (disambiguation).
Not to be confused with Pyrolysis.
Pyrrolysine
Names
IUPAC name
Pyrrolysine
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 Y
    Key: ZFOMKMMPBOQKMC-KXUCPTDWSA-N Y
  • 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 YN ?)
Infobox references
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