D3876
2′-Deoxyuridine 5′-monophosphate disodium salt
Sigma Grade
Synonym(s):
dUMP
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All Photos(4)
About This Item
Linear Formula:
C9H11N2O8PNa2
CAS Number:
Molecular Weight:
352.15
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Recommended Products
biological source
synthetic (organic)
Quality Level
grade
Sigma Grade
Assay
≥98% (HPLC)
form
powder
storage temp.
−20°C
SMILES string
[Na].OC1CC(OC1COP(O)(O)=O)N2C=CC(=O)NC2=O
InChI
1S/C9H13N2O8P.Na.H/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17;;/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17);;
InChI key
WXIVKKBDJOCRNB-UHFFFAOYSA-N
General description
2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) is a substrate for thymidylate synthase and is converted to deoxythymidine monophosphate (dTMP).
Application
2′-Deoxyuridine 5′-monophosphate (dUMP) is used by the enzyme thymidylate synthetase (TS) (EC 2.1.1.45) for the de novo production of dTMP. dUMP is used as the reference substrate in studies of dUMP analogues in potential chemotherapy applications.
2′-Deoxyuridine 5′-monophosphate disodium salt has been used:
- in ultraperformance liquid chromatography-tandem mass spectrometry (UPLC/MS/MS) assay
- to stimulate proliferation of peripheral blood mononuclear cell (PBMCs) exposed to influenza virus antigen
- in thymidylate synthase activity assay Helicobacter pylori
Biochem/physiol Actions
2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) conversion to pyrimidine is inhibited by methotrexate. The inhibition of dUMP to deoxythymidine monophosphate (dTMP) at the methylation step is a key in controlling bacterial and eukaryotic cell growth.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Peter S Ludwig et al.
European journal of medicinal chemistry, 40(5), 494-504 (2005-05-17)
Amphiphilic anticancer prodrugs of 5'-fluoro-2'-deoxyuridine-5'-monophosphate (5-FdUMP) were synthesized according to the hydrogen phosphonate method by coupling lipophilic cytosine derivatives or a phospholipid with 5-fluoro-2'-deoxyuridine (5-FdU). Studies within the in vitro Anticancer Screen Program of the National Cancer Institute have demonstrated
Zachary Newby et al.
Biochemistry, 45(24), 7415-7428 (2006-06-14)
The enzyme thymidylate synthase (TS) catalyzes the reductive methylation of 2'-deoxyuridine 5'-monophosphate (dUMP) to 2'-deoxythymidine 5'-monophosphate. Using kinetic and X-ray crystallography experiments, we have examined the role of the highly conserved Tyr-261 in the catalytic mechanism of TS. While Tyr-261
Abalo Chango et al.
Medical principles and practice : international journal of the Kuwait University, Health Science Centre, 18(2), 81-84 (2009-02-11)
To develop a method for the simultaneous measurement of 5-methylcytosine (5-metC) and 2'-deoxyuridine monophosphate (dU). Genomic DNA was extracted from the HepG2 cell line grown in experimental complete medium or in folate-depleted medium. Samples were treated with RNAse A and
Dimitri Topalis et al.
The FEBS journal, 272(24), 6254-6265 (2005-12-13)
Anti-poxvirus therapies are currently limited to cidofovir [(S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine], but drug-resistant strains have already been characterized. In the aim of finding a new target, the thymidylate (TMP) kinase from vaccinia virus, the prototype of Orthopoxvirus, has been overexpressed in Escherichia coli
Xiaoli Zhang et al.
Protein and peptide letters, 19(11), 1225-1230 (2012-04-20)
ThyX, a flavin-dependent thymidylate synthase that is involved in the synthesis of dTMP from dUMP, is a promising target for the development of novel antibacterial drugs that aimed at blocking the biosynthesis of dTMP, one of the building blocks of
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