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D3876

Sigma-Aldrich

2′-Deoxyuridine 5′-monophosphate disodium salt

Sigma Grade

Synonyme(s) :

dUMP

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About This Item

Formule linéaire :
C9H11N2O8PNa2
Numéro CAS:
42155-08-8
Poids moléculaire :
352.15
Numéro CE :
255-687-1
Numéro MDL:
MFCD00065282
Code UNSPSC :
41106305
ID de substance PubChem :
24893787
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Niveau de qualité

200

Qualité

Sigma Grade

Pureté

≥98% (HPLC)

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

[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);;

Clé InChI

WXIVKKBDJOCRNB-UHFFFAOYSA-N

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Dietary nucleotides and human immune cells. II. Modulation of PBMC growth and cytokine secretion
Holen E, et al.
Nutrition, 21(10), 1003-1009 (2005)
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
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
Glyn R Hemsworth et al.
The Journal of biological chemistry, 286(18), 16470-16481 (2011-04-02)
Members of the Leishmania genus are the causative agents of the life-threatening disease leishmaniasis. New drugs are being sought due to increasing resistance and adverse side effects with current treatments. The knowledge that dUTPase is an essential enzyme and that
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
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