957-75-5
Chemical Structure
5-Bromouridine
- CAS No.: 957-75-5
- Formula:C9H11BrN2O6
- Molecular Weight:323.10
IUPAC Name: 5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChIKey: AGFIRQJZCNVMCW-UAKXSSHOSA-N
SMILES: O[C@H]1[C@@H](O)[C@H](N2C(NC(C(Br)=C2)=O)=O)O[C@@H]1CO
Biological Activity: 5-Bromouridine is a brominated uridine nucleoside. The triphosphate form of 5-Bromouridine, 5BrdUTP, can substitute for TTP as a substrate for DNA polymerase and be incorporated into nascent DNA strands, rendering the resulting 5-bromouridine-labeled DNA photosensitive to 300 nm UV irradiation; upon UV irradiation, the 5BrdU signal decreases and dU is generated, accompanied by DNA strand breaks and cross-link formation. 5-Bromouridine is useful for studies on nucleoside structure and halogenated nucleoside-labeled nucleic acids[1][2].
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5-Bromouridine | 99.89% | 5-Bromouridine is a brominated uridine nucleoside. The triphosphate form of 5-Bromouridine, 5BrdUTP, can substitute for TTP as a substrate for DNA polymerase and be incorporated into nascent DNA strands, rendering the resulting 5-bromouridine-labeled DNA photosensitive to 300 nm UV irradiation; upon UV irradiation, the 5BrdU signal decreases and dU is generated, accompanied by DNA strand breaks and cross-link formation. 5-Bromouridine is useful for studies on nucleoside structure and halogenated nucleoside-labeled nucleic acids. | ||||||||||||||||||||
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References
- [1]. Iball J, et al. The Crystal and Molecular Structures of 5-Bromo-2′-Deoxyuridine and 5-Bromouridine. Proc R Soc Lond A. 1966;295(1442):320-333.
- [2]. Michalska B, et al. PCR synthesis of double stranded DNA labeled with 5-bromouridine. A step towards finding a bromonucleoside for clinical trials. Journal of pharmaceutical and biomedical analysis. 2011 Dec 05;56(4):671-7.
