Structure via PubChem · Public domain (PubChem)
L-pyrrolysine
Sign in to saveAlso known as N6-((2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl)-L-lysine, N6-(4-methyl-1,2-didehydropyrrolidine-5-carboxyl)-L-lysine, monomethylamine methyltransferase cofactor lysine adduct, pyrrolysine, (2S)-2-amino-6-[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl]aminohexanoic acid
Pyrrolysine (symbol Pyl or O), encoded by the "amber" stop codon UAG, is a proteinogenic amino acid that is used in some methanogenic archaea and in bacteria. It consists of lysine with a 4-methylpyrroline-5-carboxylate in amide linkage with the εN of the lysine. Its pyrroline side-chain is similar to that of lysine in being basic and positively charged at neutral pH.
Chemical data
- Formula
- C12H21N3O3
- Molecular weight
- 255.31 g/mol
- IUPAC name
- (2S)-2-amino-6-[[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrole-2-carbonyl]amino]hexanoic acid
- SMILES
- C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@@H](C(=O)O)N
- InChIKey
- ZFOMKMMPBOQKMC-KXUCPTDWSA-N
- XLogP
- -2.8
- Polar surface area
- 105 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- carbon
- Mass
- 255.158
Show 4 more facts
- chemical formula
- C₁₂H₂₁N₃O₃
- isomeric SMILES
- C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@@H](C(=O)O)N
- canonical SMILES
- CC1CC=NC1C(=O)NCCCCC(C(=O)O)N
- Commons category
- Pyrrolysine
via Wikidata · CC0
~12 min read
Encyclopedic overview
12 sectionsContents
- Genetics
- Synthesis
- Catalytic function
- Genetic coding
- Use in bioengineering
- Evolution
- Evolution of pyrrolysine methyltransferases
- Non-methyltransferase function
- Potential for an alternative translation
- References
- Further reading
- External links
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464378022 | ImageFile1 = Pyrrolysine.svg | ImageSize1 = 240px | ImageFile2 = Pyrrolysine-from-PDB-3D-bs-17.png | ImageSize2 = 240px | IUPACName = Pyrrolysine |SystematicName=N6-{[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]carbonyl}-L-lysine | OtherNames = (2S)-2-amino-6-{[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrole-2-carbonyl]-amino}-hexanoic acidN6-(4-methyl-1,2-didehydropyrrolidine-5-carboxyl)-L-lysinemonomethylamine methyltransferase cofactor lysine adduct | Section1 = | Section2 = }} Pyrrolysine (symbol Pyl or O), encoded by the "amber" stop codon UAG, is a proteinogenic amino acid that is used in some methanogenic archaea and in bacteria. It consists of lysine with a 4-methylpyrroline-5-carboxylate in amide linkage with the εN of the lysine. Its pyrroline side-chain is similar to that of lysine in being basic and positively charged at neutral pH.
==Genetics== Nearly all genes are translated using only 20 standard amino acid building blocks. Two unusual genetically encoded amino acids are selenocysteine and pyrrolysine. Pyrrolysine was discovered in 2002 at the active site of methyltransferase enzyme from a methane-producing archeon, Methanosarcina barkeri. This amino acid is encoded by UAG (normally a stop codon), and its synthesis and incorporation into protein is mediated via the biological machinery encoded by the pylTSBCD cluster of genes.
Excerpted from Wikipedia’s “L-pyrrolysine” article, available under the CC BY-SA 4.0 licence.