11544
2′-Azido-2′-deoxyuridine
≥98.0% (N)
Synonym(s):
N3-dU
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About This Item
Empirical Formula (Hill Notation):
C9H11N5O5
CAS Number:
Molecular Weight:
269.21
Beilstein/REAXYS Number:
4204828
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
biological source
synthetic
assay
≥98.0% (N)
form
powder
mp
149-153 °C
storage temp.
2-8°C
SMILES string
OC[C@H]1O[C@H]([C@H](N=[N+]=[N-])[C@@H]1O)N2C=CC(=O)NC2=O
InChI
1S/C9H11N5O5/c10-13-12-6-7(17)4(3-15)19-8(6)14-2-1-5(16)11-9(14)18/h1-2,4,6-8,15,17H,3H2,(H,11,16,18)/t4-,6-,7-,8-/m1/s1
InChI key
MRUKYOQQKHNMFI-XVFCMESISA-N
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Application
2′-Azido-2′-deoxyuridine (N3-dU) upon phosphorylation to 2′-azido-2′-deoxyuridine 5′-diphosphate (N3dUDP) becomes a mechanistic inhibitor of bacterial ribonucleoside diphosphate reductase (RDPR). N3-dU has recently been evaluated for its potential use as a sensitive multi-spectroscopic probe for nucleic acids
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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S Salowe et al.
Biochemistry, 32(47), 12749-12760 (1993-11-30)
Ribonucleotide reductase (RDPR) from Escherichia coli is composed of two subunits, R1 and R2, and catalyzes the conversion of nucleotides to deoxynucleotides. The mechanism of inactivation of RDPR by 2'-azido-2'-deoxynucleoside 5'-diphosphate (N3UDP) has been examined using a variety of isotopically
Béatrice Roy et al.
Biochemical pharmacology, 68(4), 711-718 (2004-07-28)
In this paper, the enantioselectivity of ribonucleotide reductase (RNR, EC 1.17.4.1), a pivotal enzyme involved in DNA biosynthesis, was studied using the beta-d and beta-l stereoisomers of 2'-azido-2'-deoxynucleosides of uracil and cytosine. The corresponding 5'-diphosphate derivatives in the d-configuration have
Matthew J Tucker et al.
Physical chemistry chemical physics : PCCP, 13(6), 2237-2241 (2010-12-01)
The vibrations in the azido-, N(3), asymmetric stretching region of 2'-azido-2'-deoxyuridine (N(3)dU) are examined by two-dimensional infrared spectroscopy. In water and tetrahydrofuran (THF), the spectra display a single sharp diagonal peak that shows solvent sensitivity. The frequency-frequency correlation time in
S P Salowe et al.
Biochemistry, 26(12), 3408-3416 (1987-06-16)
Ribonucleoside diphosphate reductase (RDPR) from Escherichia coli was completely inactivated by 1 equiv of the mechanism-based inhibitor 2'-azido-2'-deoxyuridine 5'-diphosphate (N3UDP). Incubation of RDPR with [3'-3H]N3UDP resulted in 0.2 mol of 3H released to solvent per mole of enzyme inactivated, indicating
S H Kang et al.
Nucleosides & nucleotides, 17(6), 1077-1088 (1998-08-26)
2'-Azido-2'-deoxyuridine and 2'-azido-2'-deoxycytidine were evaluated for their inhibitory activity against ribonucleotide reductase and for subsequent cell growth inhibition. Their mono- and di-phosphates were synthesized and their inhibitory activities against the reductase were also determined in a permeabilized cell system, along
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