5-Bromouridine

5-Bromouridine
Names
	IUPAC name 5-Bromouridine
	Systematic IUPAC name 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-bromoimidazole-2,4(1H,3H)-dione
	Other names 5-Bromouracil ribonucleoside; 1-β-Ribofuranosyl-5-bromo-uracil; 5-Bromouridin
Identifiers
CAS Number	957-75-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	BrUrd
Beilstein Reference	33664
ChEBI	CHEBI:20553;
ChemSpider	82616;
ECHA InfoCard	100.012.260
EC Number	213-486-6;
PubChem CID	91494;
UNII	KEY8PG1BRC ;
CompTox Dashboard (EPA)	DTXSID401317210 ;
	InChI InChI=1S/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1 Key: AGFIRQJZCNVMCW-UAKXSSHOSA-N; InChI=1/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1 Key: AGFIRQJZCNVMCW-UAKXSSHOBS;
	SMILES BrC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO;
Properties
Chemical formula	C9H11BrN2O6
Molar mass	323.099 g·mol−1
Appearance	Crystalline, white solid
Density	2.043 g/cm3
Melting point	180 to 182 °C (356 to 360 °F; 453 to 455 K) (decomposes)
Chiral rotation ([α]D)	[α]22/D −11°, c = 2 in H2O
Hazards
Autoignition; temperature	Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), Hydrogen bromide gas
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Bromouridine (abbreviated BrUrd, 5BrU, br5Urd or rarely the one letter code B)^[2] is a uridine derivative with a bromo substituent at the fifth carbon.^[3] BrUrd is incorporated into RNA and can be detected immunocytochemically and analysed by cytometry. It causes DNA damage through base substitution and increases the number of mutations.^[4]

^ 5-bromouridine in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2012)
^ IUPAC-IUB Commission on Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents". Biochemistry. 9 (20): 4022–4027. doi:10.1021/bi00822a023.
^ CSID:82616, http://www.chemspider.com/Chemical-Structure.82616.html (accessed 22:51, Oct 19, 2012)
^ "5-bromouridine (CHEBI:20553)." EBI.ac.uk. European Bioinformatics Institute, 30 Nov. 2010. Web. 26 Oct. 2012.<http://www.ebi.ac.uk/chebi/advancedSearchFT.do;jsessionid=29B3462C81CE2E1F80223B50A927F832?chebiId=20553&structureSearchMethod=substructure>

[1] 5-bromouridine in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2012)

[2] IUPAC-IUB Commission on Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents". Biochemistry. 9 (20): 4022–4027. doi:10.1021/bi00822a023.

[3] CSID:82616, http://www.chemspider.com/Chemical-Structure.82616.html (accessed 22:51, Oct 19, 2012)

[4] "5-bromouridine (CHEBI:20553)." EBI.ac.uk. European Bioinformatics Institute, 30 Nov. 2010. Web. 26 Oct. 2012.<http://www.ebi.ac.uk/chebi/advancedSearchFT.do;jsessionid=29B3462C81CE2E1F80223B50A927F832?chebiId=20553&structureSearchMethod=substructure>

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