MetaCyc Compound: L-pyrrolysine

Synonyms: pyrrolysine, (2S)-2-amino-6-[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl]aminohexanoic acid, N6-(4-methyl-1,2-didehydropyrrolidine-5-carboxyl)-L-lysine, N6-((2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl)-L-lysine, N6-(4-methyl-δ-1-pyrroline-5-carboxyl)-L-lysine

Superclasses: an amino acid or its derivative an amino acid an alpha amino acid a non-standard alpha amino acid

Pyrrolysine (Pyl or O) is a naturally occurring, genetically coded amino acid. It is used by some methanogenic archaea (and one known bacterium) in several methyltransferases that are involved in methyl transfer from methylated amine compounds to coenzyme M, part of the methanogenesis pathways from these compounds (see methylamine--corrinoid protein Co-methyltransferase, dimethylamine--corrinoid protein Co-methyltransferase and trimethylamine--corrinoid protein Co-methyltransferase). These enzymes catalyze the transfer of the methyl group to dedicated corrinoid proteins. It is believed that the pyrrolysine ring is involved in positioning and displaying the methyl group for attack by the corrinoid cofactor [Hao02].

Pyrrolysine is encoded in mRNA by the UAG codon, which in most organisms is the 'amber' stop codon. Its incorporation into proteins requires two genes - the pylT gene, which encodes an unusual transfer RNA (tRNA) with a CUA anticodon, and the pylS gene, which encodes a class II aminoacyl-tRNA synthetase that charges the pylT-derived tRNA with pyrrolysine. Reviewed in [Gaston11].

Chemical Formula: C12H21N3O3

Molecular Weight: 255.32 Daltons

Monoisotopic Molecular Weight: 255.158291556 Daltons

L-pyrrolysine compound structure

SMILES: CC1([CH](C(=O)NCCCCC([N+])C([O-])=O)N=CC1)

InChI: 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


Unification Links: ChEBI:58499 , KEGG:C16138 , PubChem:25244363

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 127.54354 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
ATP + L-pyrrolysine + a tRNApyl + H+ → AMP + an L-pyrrolysyl-[tRNAPyl] + diphosphate

Reactions known to produce the compound:

L-pyrrolysine biosynthesis :
(2R,3R)-3-methylornithinyl-N6-lysine + NAD+L-pyrrolysine + ammonium + NADH + 2 H+

Not in pathways:
(2R,3R)-3-methylglutamyl-5-semialdehyde-N6-lysine → L-pyrrolysine + H+ + H2O

Not in pathways:
amino acids(n) + H2O → amino acids(n-1) + an α amino acid
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a protein + H2O → a protein + an α amino acid

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Revised 13-Dec-2011 by Caspi R , SRI International
Revised 13-Feb-2012 by Fulcher CA , SRI International


Gaston11: Gaston MA, Jiang R, Krzycki JA (2011). "Functional context, biosynthesis, and genetic encoding of pyrrolysine." Curr Opin Microbiol 14(3);342-9. PMID: 21550296

Hao02: Hao B, Gong W, Ferguson TK, James CM, Krzycki JA, Chan MK (2002). "A new UAG-encoded residue in the structure of a methanogen methyltransferase." Science 296(5572);1462-6. PMID: 12029132

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Thu Mar 26, 2015, biocyc12.