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D3876

2′-Deoxyuridine 5′-monophosphate disodium salt

≥98% (HPLC), synthetic (organic), powder

Synonym(s):

dUMP

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About This Item

Linear Formula:
C9H11N2O8PNa2
CAS Number:
42155-08-8
Molecular Weight:
352.15
EC Number:
255-687-1
MDL number:
MFCD00065282
UNSPSC Code:
41106305
PubChem Substance ID:
24893787
NACRES:
NA.51

Key Documents

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Product Name

2′-Deoxyuridine 5′-monophosphate disodium salt, Sigma Grade

biological source

synthetic (organic)

Quality Level

200

grade

Sigma Grade

Assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

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

Related Categories

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000474518
0000474518
0000411514
0000411514
0000374876

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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
Biochemistry: Anchors away.
Maria Paola Costi et al.
Nature, 458(7240), 840-841 (2009-04-17)
Przemysław Ziemkowski et al.
Biochemical and biophysical research communications, 362(1), 37-43 (2007-08-19)
A series of 2'-fluoro-substituted dUMP/FdUMP analogues were synthesized, their interaction with human recombinant thymidylate synthase investigated, and structural (1)H and (19)F NMR study of the corresponding nucleosides performed. While 2'-F-dUMP (fluorine in the "down" configuration), in striking contrast to 2'-F-ara-UMP
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
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