Pirolohinolin hinon

Pirolohinolin hinon
Identifikacija
CAS registarski broj	72909-34-3
PubChem	1024
ChemSpider	997
KEGG	C00113
MeSH	PQQ+Cofactor
ChEBI	18315
Jmol-3D slike	Slika 1
SMILES
	c1c2c([nH]c1C(=O)O)-c3c(cc(nc3C(=O)C2=O)C(=O)O)C(=O)O
InChI
	InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24) ; Kod: MMXZSJMASHPLLR-UHFFFAOYSA-N InChI=1/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24); Kod: MMXZSJMASHPLLR-UHFFFAOYAP
Svojstva
Molekulska formula	C14H6N2O8
Molarna masa	330.21 g mol−1
Gustina	1,963 g/cm3
Opasnost
Tačka paljenja	569,8 °C
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Pirolohinolin hinon (PQQ) je redoks kofaktor kod bakterija .^[5]^[6]^[7]^[8] PQQ je prostetička grupa u metanolnoj dehidrogenazi metilotrofa, kao što je bakterijska vrsta Acetobacter.^[9]

Enzimi koji sadrže PQQ se nazivaju hinoproteini. Glukozna dehidrogenaza, jedan od hinoproteina, se koristi kao glukozni senzor. Utvrđeno je da PQQ stimuliše rast bakterija.^[10] Osim toga, on ima antioksidansno i neuroprotektivno dejstvo.^[11]

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.^[12]

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.
↑ 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. DOI:10.1038/280843a0. PMID 471057.
↑ 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. DOI:10.1016/0006-291X(79)92018-7. PMID 222269.
↑ 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. DOI:10.1016/0014-5793(81)81114-3. PMID 6793395.
↑ 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.

Vanjske veze

Portal Hemija

[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.

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

[6] 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.

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

[8] 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. DOI:10.1016/0006-291X(79)92018-7. PMID 222269.

[9] 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. DOI:10.1016/0014-5793(81)81114-3. PMID 6793395.

[10] 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.

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

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

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]