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
Standard Gibbs Free Energy of Change Formation (ΔfG'° in kcal/mol): 127.54354 [Latendresse13]
Reactions known to consume the compound:
Reactions known to produce the compound:
In Reactions of unknown directionality:
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