59090-48-1

Basic information

• Product Name: 5-azidomethyl-2'-deoxyuridine
• Synonyms: 5-azidomethyl-2'-deoxyuridine
• CAS NO: 59090-48-1
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 0
• Mol File: 59090-48-1.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: Soluble in Water, alcohols, DMSO, DMF
• CAS DataBase Reference: 5-azidomethyl-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-azidomethyl-2'-deoxyuridine(59090-48-1)
• EPA Substance Registry System: 5-azidomethyl-2'-deoxyuridine(59090-48-1)

Safety Data

• Hazardous Substances Data: 59090-48-1(Hazardous Substances Data)

Usage

General Description

5-azidomethyl-2'-deoxyuridine is a modified nucleoside analog that contains an azide group at the 5' position of the sugar moiety. It is commonly used in chemical biology and bioorthogonal chemistry applications as a nucleoside analogue that can be incorporated into DNA during synthesis. 5-azidomethyl-2'-deoxyuridine has been used in several studies to probe the dynamics and interactions of DNA, as well as to study the mechanisms of DNA repair and replication. Additionally, 5-azidomethyl-2'-deoxyuridine has also been utilized in the development of new diagnostic tools for the imaging and detection of DNA in biological systems. Overall, this compound plays a critical role in understanding the biology of DNA and developing new tools for biomedical research.

InChI:InChI=1/C10H13N5O5/c11-14-12-2-5-3-15(10(19)13-9(5)18)8-1-6(17)7(4-16)20-8/h3,6-8,11,16-17H,1-2,4H2/p+1

Upstream product

• 72274-20-5 3′,5′-di-O-acetyl-5-azidomethyl-2′-deoxyuridine 
• 35898-30-7 3',5'-di-O-benzoylthymidine 
• 291525-17-2 3′,5′-bis-O-(tert-butyldimethylsilyl)-5-bromomethyl-2'-deoxyuridine 
• 823790-97-2 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(azidomethyl)-2'-deoxyuridine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 50-89-5 thymidine 
• 5116-24-5 2'-deoxy-5-(hydroxymethyl)uridine 
• 58589-18-7 3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 
• 6979-97-1 3',5'-diacetylthymidine 
• 825649-02-3 5-(N-methoxymethylamine)-2'-deoxyuridine 

Downstream Products

• 1620130-62-2 5'-O-(4,4'-dimethoxytriphenylmethyl)-5-(4-methylchromen-2-one-1,2,3-triazol-1-yl)methyl-2'-deoxyuridine 
• 263758-82-3 {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester 
• 263758-81-2 {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester 
• 263712-30-7 {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine S-phenyl ester 
• 886578-12-7 6-[3-O-(tert-butyl(dimethyl)silyl)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3,4-dihydropyrimido[4,5-d]pyrimidine-2,7(1H,6H)-dione 
• 823791-02-2 3'-O-(tert-butyl(dimethyl)silyl)-5'-O-(4,4'-dimethoxytrityl)-5-(azidomethyl)deoxycytidine 
• 823791-01-1 3'-O-(tert-butyl(dimethyl)silyl)-5'-O-(4,4'-dimethoxytrityl)-5-(azidomethyl)deoxyuridine 
• 886578-13-8 6-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3,4-dihydropyrimido[4,5-d]pyrimidine-2,7(1H,6H)-dione 
• 137552-29-5 5-(azidomethyl)-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyuridine 
• 70465-55-3 5-(aminomethyl)-2'-deoxyuridine 

Relevant articles and documents

Synthesis of a new analog of thymidine for in vivo non-radioactive labeling of DNA

The introduction of 6-(p-bromobenzoylamino)caproyl radical in the methyl group of 2'-O-deoxythymidine is described. In vivo incorporation of this nucleoside to DNA was determined using a monoclonal antibody that recognized the radical.

Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells

Two classes of azido-modified pyrimidine nucleosides were synthesized as potential radiosensitizers; one class is 5-azidomethyl-2′-deoxyuridine (AmdU) and cytidine (AmdC), while the second class is 5-(1-azidovinyl)-2′-deoxyuridine (AvdU) and cytidine (AvdC). The addition of radiation-produced electrons to C5-azido nucleosides leads to the formation of π-aminyl radicals followed by facile conversion to σ-iminyl radicals either via a bimolecular reaction involving intermediate α-azidoalkyl radicals in AmdU/AmdC or by tautomerization in AvdU/AvdC. AmdU demonstrates effective radiosensitization in EMT6 tumor cells.

One-step to get 5-azidomethyl-2′-deoxyuridine from 5-hydroxymethyl-2′-deoxyuridine and detection of it through click reaction

Nowadays a few ways to synthesize 5-azidomethyl-2′-deoxyuridine from 5-hydroxymethyl-2′-deoxyuridine have been reported. But none of them was one-step. And many of them need to protect the hydroxyl group on the pentose ring. The detection of 5-hydroxymethyl-2′-deoxyuridine is also very important in many biological processes. However few fluorescence detection strategies have been tried to do this. Herein, we reported a one-step protocol to synthesize 5-azidomethyl-2′-deoxyuridine, which was then used for detecting 5-hydroxymethyl-2′-deoxyuridine through a click reaction.