Pyrrolysine

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
CAS Number	448235-52-7 ;
3D model (JSmol)	Interactive image; Zwitterion: Interactive image;
ChEBI	CHEBI:21860 ;
ChemSpider	4574156 ;
KEGG	C16138 ;
PubChem CID	5460671;
UNII	H3214Y96LP ;
CompTox Dashboard (EPA)	DTXSID70420110 ;
	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 Key: ZFOMKMMPBOQKMC-KXUCPTDWSA-N ; 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;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

Pyrrolysine (symbol Pyl or O^[2]), encoded by the 'amber' stop codon UAG, is a proteinogenic amino acid that is used in some methanogenic archaea and in bacteria.^[3]^[4] 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.^[5]^[6]

^ 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.
^ "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.
^ 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.
^ 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.
^ Hao, Bing; Gong; Ferguson; James; Krzycki; Chan (2002-05-24). "A New UAG-Encoded Residue in the Structure of a Methanogen Methyltransferase". Science. 296 (5572): 1462–1466. Bibcode:2002Sci...296.1462H. doi:10.1126/science.1069556. PMID 12029132. S2CID 35519996.
^ Soares, J. A.; Zhang, L; Pitsch, R. L.; Kleinholz, N. M.; Jones, R. B.; Wolff, J. J.; Amster, J; Green-Church, K. B.; Krzycki, J. A. (2005-11-04). "The residue mass of L-pyrrolysine in three distinct methylamine methyltransferases". The Journal of Biological Chemistry. 280 (44): 36962–36969. doi:10.1074/jbc.M506402200. PMID 16096277.

[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.

[pmid20847933-4] 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.

[Hao-5] Hao, Bing; Gong; Ferguson; James; Krzycki; Chan (2002-05-24). "A New UAG-Encoded Residue in the Structure of a Methanogen Methyltransferase". Science. 296 (5572): 1462–1466. Bibcode:2002Sci...296.1462H. doi:10.1126/science.1069556. PMID 12029132. S2CID 35519996.

[Soares-6] Soares, J. A.; Zhang, L; Pitsch, R. L.; Kleinholz, N. M.; Jones, R. B.; Wolff, J. J.; Amster, J; Green-Church, K. B.; Krzycki, J. A. (2005-11-04). "The residue mass of L-pyrrolysine in three distinct methylamine methyltransferases". The Journal of Biological Chemistry. 280 (44): 36962–36969. doi:10.1074/jbc.M506402200. PMID 16096277.

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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
CAS Number	448235-52-7^Y
3D model (JSmol)	Interactive image Zwitterion: Interactive image
ChEBI	CHEBI:21860^N
ChemSpider	4574156^Y
KEGG	C16138^Y
PubChem CID	5460671
UNII	H3214Y96LP^Y
CompTox Dashboard (EPA)	DTXSID70420110
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^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
SMILES 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
Chemical formula	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