Pirolohinolin hinon

Pirolohinolin hinon
Identifikacija
CAS broj	72909-34-3 ;
3D model (Jmol)	interaktivna slika;
ChEBI	CHEBI:18315 ;
ChemSpider	997 ;
KEGG	C00113 ;
MeSH	PQQ Cofactor
PubChem C ID	1024;
	SMILES c1c2c([nH]c1C(=O)O)-c3c(cc(nc3C(=O)C2=O)C(=O)O)C(=O)O; ; ; ; ; ;
Svojstva
Hemijska formula	C14H6N2O8
Molarna masa	330,21 g·mol−1
Gustina	1,963 g/cm3
Opasnosti
Tačka paljenja	569,8 °C
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

Pirolohinolin hinon (PQQ) je redoks kofaktor kod bakterija .^[4]^[5]^[6]^[7] PQQ je prostetička grupa u metanolnoj dehidrogenazi metilotrofa, kao što je bakterijska vrsta Acetobacter.^[8]

Enzimi koji sadrže PQQ se nazivaju hinoproteini. Glukozna dehidrogenaza, jedan od hinoproteina, se koristi kao glukozni senzor. Utvrđeno je da PQQ stimuliše rast bakterija.^[9] Osim toga, on ima antioksidansno i neuroprotektivno dejstvo.^[10]

PQQ biosinteza kod bakterija počinje sa proteinskom biosintezom kojom se formira kratki peptid, PqqA, na ribozomu. Svi atomi u PQQ su izvedeni iz glutaminske kiseline i tirozina u PqqA, koji se povezuju posrestvom radikalnog SAM enzima PqqE.^[11]

Reference

^ 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.
^ 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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ 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.
^ Hauge JG (1964). „Glucose dehydrogenase of bacterium anitratum: an enzyme with a novel prosthetic group”. J Biol Chem. 239: 3630—9. PMID 14257587.
^ Anthony C, Zatman LJ (1967). „The microbial oxidation of methanol. The prosthetic group of the alcohol dehydrogenase of Pseudomonas sp. M27: a new oxidoreductase prosthetic group”. Biochem J. 104 (3): 960—9. PMC 1271238 . PMID 6049934.
^ Salisbury SA, Forrest HS, Cruse WB, Kennard O (1979). „A novel coenzyme from bacterial primary alcohol dehydrogenases”. Nature. 280 (5725): 843—4. PMID 471057. doi:10.1038/280843a0.
^ Westerling J, Frank J, Duine JA (1979). „The prosthetic group of methanol dehydrogenase from Hyphomicrobium X: electron spin resonance evidence for a quinone structure”. Biochem Biophys Res Commun. 87 (3): 719—24. PMID 222269. doi:10.1016/0006-291X(79)92018-7.
^ Ameyama M, Matsushita K, Ohno Y, Shinagawa E, Adachi O (1981). „Existence of a novel prosthetic group, PQQ, in membrane-bound, electron transport chain-linked, primary dehydrogenases of oxidative bacteria”. FEBS Lett. 130 (2): 179—83. PMID 6793395. doi:10.1016/0014-5793(81)81114-3.
^ Ameyama M, Matsushita K, Shinagawa E, Hayashi M, Adachi O (1988). „Pyrroloquinoline quinone: excretion by methylotrophs and growth stimulation for microorganisms”. BioFactors. 1 (1): 51—3. PMID 2855583.
^ Rucker R, Chowanadisai W, Nakano M (2009). „Potential physiological importance of pyrroloquinoline quinone”. Altern Med Rev. 14 (3): 179—83.
^ Puehringer S, Metlitzky M, Schwarzenbacher R (2008). „The pyrroloquinoline quinone biosynthesis pathway revisited: a structural approach.”. BMC Biochem. 9: 8. PMID 18371220.

Spoljašnje veze

[1] 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.

[2] 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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[3] 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.

[4] Hauge JG (1964). „Glucose dehydrogenase of bacterium anitratum: an enzyme with a novel prosthetic group”. J Biol Chem. 239: 3630—9. PMID 14257587.

[5] Anthony C, Zatman LJ (1967). „The microbial oxidation of methanol. The prosthetic group of the alcohol dehydrogenase of Pseudomonas sp. M27: a new oxidoreductase prosthetic group”. Biochem J. 104 (3): 960—9. PMC 1271238 . PMID 6049934.

[6] Salisbury SA, Forrest HS, Cruse WB, Kennard O (1979). „A novel coenzyme from bacterial primary alcohol dehydrogenases”. Nature. 280 (5725): 843—4. PMID 471057. doi:10.1038/280843a0.

[7] Westerling J, Frank J, Duine JA (1979). „The prosthetic group of methanol dehydrogenase from Hyphomicrobium X: electron spin resonance evidence for a quinone structure”. Biochem Biophys Res Commun. 87 (3): 719—24. PMID 222269. doi:10.1016/0006-291X(79)92018-7.

[8] Ameyama M, Matsushita K, Ohno Y, Shinagawa E, Adachi O (1981). „Existence of a novel prosthetic group, PQQ, in membrane-bound, electron transport chain-linked, primary dehydrogenases of oxidative bacteria”. FEBS Lett. 130 (2): 179—83. PMID 6793395. doi:10.1016/0014-5793(81)81114-3.

[9] Ameyama M, Matsushita K, Shinagawa E, Hayashi M, Adachi O (1988). „Pyrroloquinoline quinone: excretion by methylotrophs and growth stimulation for microorganisms”. BioFactors. 1 (1): 51—3. PMID 2855583.

[10] Rucker R, Chowanadisai W, Nakano M (2009). „Potential physiological importance of pyrroloquinoline quinone”. Altern Med Rev. 14 (3): 179—83.

[11] Puehringer S, Metlitzky M, Schwarzenbacher R (2008). „The pyrroloquinoline quinone biosynthesis pathway revisited: a structural approach.”. BMC Biochem. 9: 8. PMID 18371220.

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