Pirolizin

Pirolizin
	N6-{[(2R,3R)-3-metil-3,4-dihidro-2H-pirol-2-il]karbonilL-lizin
Identifikacija
CAS registarski broj	448235-52-7
PubChem	5460671
ChemSpider	4574156
KEGG	C16138
ChEBI	58499
Jmol-3D slike	Slika 1
SMILES
	O=C(NCCCC[C@@H](C(=O)O)N)[C@@H]1/N=C\C[C@H]1C
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 ; Kod: 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; Kod: ZFOMKMMPBOQKMC-KXUCPTDWBO
Svojstva
Molekulska formula	C12H21N3O3
Molarna masa	255.31 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Pirolizin (Pyl, O) se javlja u prirodi kao gentički kodirana aminokiselina koju koriste pojedine metanogeniske arheje kao i neke bakterije. On se javlja u enzimima koji učestvuju u delju njihovog metabolizma kojim se formira metan. Pirolizin je sličan lizinu, ali ima dodatni pirolinski prsten vezan na kraju lizinskog bočnog ostatka. Postoje specifična tRNK i aminoacil tRNK sintetaza za pirolizin. One formiraju deo neuobičajenog genetičkog koda tih organizama. Pirolizin se smatra dvadesetdrugom proteinogenom aminokiselinom.

Zajednički nomenklaturni komiteti IUPAC-a/IUBMB-a su zvanično preporučili oznake Pyl i O za pirolizin.

Struktura

Na osnovu kristalografskih^[5] i MALDI maseno spektrometrijskih merenja, pirolizin se sastoji od 4-metilpirolin-5-karboksilata vezanog amidnom vezom za ^ϵN lizina.^[6]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Bing Hao, Weimin Gong, Tsuneo K. Ferguson, Carey M. James, Joseph A. Krzycki, Michael K. Chan (24. 05. 2002.). A New UAG-Encoded Residue in the Structure of a Methanogen Methyltransferase. 296. Science. pp. 1462–1466. DOI:10.1126/science.1069556. PMID 12029132.
↑ Jitesh A. Soares, Liwen Zhang, Rhonda L. Pitsch, Nanette M. Kleinholz, R. Benjamin Jones, Jeremy J. Wolff, Jon Amster, Kari B. Green-Church, and Joseph A. Krzycki (04. 11. 2005.). „The residue mass of L-pyrrolysine in three distinct methylamine methyltransferases”. The Journal of biological chemistry (Journal of Biological Chemistry) 280 (44): 36962–36969. DOI:10.1074/jbc.M506402200. PMID 16096277.

Literatura

John F. Atkins and Ray Gesteland (2002). „The 22nd Amino Acid”. Science 296 (5572): 1409–1410. DOI:10.1126/science.1073339. PMID 12029118.
Krzycki J (2005). „The direct genetic encoding of pyrrolysine”. Curr Opin Microbiol 8 (6): 706–712. DOI:10.1016/j.mib.2005.10.009. PMID 16256420.

Vidi još

Genetički kod
translacija
Selenocistein, 21-va genetički kodirana aminokiselina

Spoljašnje veze

Portal Hemija

Otkriće aminokiseline

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[Hao-5] Bing Hao, Weimin Gong, Tsuneo K. Ferguson, Carey M. James, Joseph A. Krzycki, Michael K. Chan (24. 05. 2002.). A New UAG-Encoded Residue in the Structure of a Methanogen Methyltransferase. 296. Science. pp. 1462–1466. DOI:10.1126/science.1069556. PMID 12029132.

[Soares-6] Jitesh A. Soares, Liwen Zhang, Rhonda L. Pitsch, Nanette M. Kleinholz, R. Benjamin Jones, Jeremy J. Wolff, Jon Amster, Kari B. Green-Church, and Joseph A. Krzycki (04. 11. 2005.). „The residue mass of L-pyrrolysine in three distinct methylamine methyltransferases”. The Journal of biological chemistry (Journal of Biological Chemistry) 280 (44): 36962–36969. DOI:10.1074/jbc.M506402200. PMID 16096277.

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p r u 20 osnovnih aminokiselina
Esencijalne aminokiseline	Izoleucin • Leucin • Lizin • Metionin • Fenilalanin • Treonin • Triptofan • Valin
Poluesencijalne aminokiseline	Arginin • Histidin
Neesencijalne aminokiseline	Alanin • Asparagin • Asparaginska kiselina • Cistein • Glutaminska kiselina • Glutamin • Glicin • Prolin • Serin • Tirozin
Druge klasifikacije	Ketogene aminokiseline • Glukogene aminokiseline
Biohemijske familije: Ugljeni hidrati (Glikozidi,Alkoholi) • Lipidi (Steroidi,Fosfolipidi,Glikolipidi,Masne kiseline,Tetrapiroli) • Proteini (Aminokiseline,Peptidi,Glikoproteini) • Nukleobaze/Nukleinske kiseline