Kjuozin

Kjuozin
	2-Amino-5-[[[(1S,4S,5R)-4,5-dihidroksi-1-ciklopent-2-enil]amino]metil]-7-[(2R,3R,4S,5R)-3,4-dihidroksi-5-(hidroksimetil)-2-tetrahidrofuranil]-1H-pirolo[3,2-e]pirimidin-4-on
Identifikacija
CAS registarski broj	57072-36-3
PubChem	42119
Jmol-3D slike	Slika 1
SMILES
	C1=C[C@@H]([C@@H]([C@H]1NCC2=CN (C3=C2C(=O)N=C(N3)N)[C@H]4[C@@H] ([C@@H]([C@H](O4)CO)O)O)O)O
InChI
	InChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16+/m0/s1 ; Kod: QQXQGKSPIMGUIZ-AEZJAUAXSA-N
Svojstva
Molekulska formula	C17H23N5O7
Molarna masa	409,39 g/mol
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Kveozin je modifikovani nukleozid koji je prisutan u pojedinim tRNK molekulima kod bakterija i eukariota.^[3]^[4] Originalno je identifikovan kod E. coli. Kveosin je prisutan u prvoj poziciji antikodona tRNA za histidin, aspartičku kiselinu, asparagin i tirozin.^[5] Prva pozicija antikodaona se sparuje sa trećom „klimavom“ pozicijom kodona, i kveozin poboljšava preciznost translacije.^[6]^[7]^[8] Sinteza kveozina počinje sa GTP-om. Kod bakterija dve klase riboprekidača regulišu gene koji učestvuju u sintezi ili transportu predveozina₁, prekursora kveozina: PreQ1-I riboprekidači i PreQ1-II riboprekidači.

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.
↑ Iwata-Reuyl D (2003). „Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA”. Bioorg. Chem. 31 (1): 24–43. DOI:10.1016/S0045-2068(02)00513-8. PMID 12697167.
↑ Morris RC, Elliott MS (2001). „Queuosine modification of tRNA: a case for convergent evolution”. Mol. Genet. Metab. 74 (1–2): 147–159. DOI:10.1006/mgme.2001.3216. PMID 11592812.
↑ Harada F, Nishimura S (1972). „Possible anticodon sequences of tRNA^His, tRNA^Asm, and tRNA^Asp from Escherichia coli B. Universal presence of nucleoside Q in the first position of the anticondons of these transfer ribonucleic acids”. Biochemistry 11 (2): 301–308. DOI:10.1021/bi00752a024. PMID 4550561.
↑ Bienz M and Kubli E (1981). „Wild-type tRNA^Tyr_G reads the TMV RNA stop codon, but Q base-modified tRNA^Tyr_Q does not”. Nature 294 (5837): 188–190. DOI:10.1038/294188a0.
↑ Meier F, Suter B, Grosjean H, Keith G, Kubli E (1985). „Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties”. EMBO J. 4 (3): 823–827. PMC 554263. PMID 2988936.
↑ Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Björk GR (2001). „Improvement of reading frame maintenance is a common function for several tRNA modifications”. EMBO J. 20 (17): 4863–4873. DOI:10.1093/emboj/20.17.4863. PMC 125605. PMID 11532950.

Literatura

Florian Klepper: Synthese der natürlichen tRNA Nukleosidmodifikationen Queuosin und Archaeosin, Dissertation, München 2007.
Florian Klepper, Eva-Maria Jahn, Volker Hickmann, Thomas Carell: „Synthese des tRNA-Nucleosids Queuosin unter Verwendung eines chiralen Allylazid-Intermediats“, Angewandte Chemie, 2007, 119 (13), pp. 2377–2379; DOI:10.1002/ange.200604579.
Florian Klepper, Eva-Maria Jahn, Volker Hickmann, Thomas Carell: „Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate“, Angewandte Chemie International Edition, 2007, 46 (13), pp. 2325–2327; DOI:10.1002/anie.200604579.

Spoljašnje veze

Portal Hemija

Kveozin Arhivirano 2012-03-12 na Wayback Machine-u
Kveozin (HMDB11596) Arhivirano 2011-07-25 na Wayback Machine-u

[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] Iwata-Reuyl D (2003). „Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA”. Bioorg. Chem. 31 (1): 24–43. DOI:10.1016/S0045-2068(02)00513-8. PMID 12697167.

[4] Morris RC, Elliott MS (2001). „Queuosine modification of tRNA: a case for convergent evolution”. Mol. Genet. Metab. 74 (1–2): 147–159. DOI:10.1006/mgme.2001.3216. PMID 11592812.

[5] Harada F, Nishimura S (1972). „Possible anticodon sequences of tRNA^His, tRNA^Asm, and tRNA^Asp from Escherichia coli B. Universal presence of nucleoside Q in the first position of the anticondons of these transfer ribonucleic acids”. Biochemistry 11 (2): 301–308. DOI:10.1021/bi00752a024. PMID 4550561.

[6] Bienz M and Kubli E (1981). „Wild-type tRNA^Tyr_G reads the TMV RNA stop codon, but Q base-modified tRNA^Tyr_Q does not”. Nature 294 (5837): 188–190. DOI:10.1038/294188a0.

[7] Meier F, Suter B, Grosjean H, Keith G, Kubli E (1985). „Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties”. EMBO J. 4 (3): 823–827. PMC 554263. PMID 2988936.

[8] Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Björk GR (2001). „Improvement of reading frame maintenance is a common function for several tRNA modifications”. EMBO J. 20 (17): 4863–4873. DOI:10.1093/emboj/20.17.4863. PMC 125605. PMID 11532950.

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