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D3876

2′-Deoxyuridine 5′-monophosphate disodium salt

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

Synonym(s):

dUMP

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CZK 6,480.00

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About This Item

Linear Formula:
C9H11N2O8PNa2
CAS Number:
42155-08-8
Molecular Weight:
352.15
NACRES:
NA.51
PubChem Substance ID:
24893787
UNSPSC Code:
41106305
EC Number:
255-687-1
MDL number:
MFCD00065282
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
−20°C

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Product Name

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

InChI key

WXIVKKBDJOCRNB-UHFFFAOYSA-N

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);;

SMILES string

[Na].OC1CC(OC1COP(O)(O)=O)N2C=CC(=O)NC2=O

biological source

synthetic (organic)

grade

Sigma Grade

assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

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1 of 4

This Item
D4001D7625U6375
2′-Deoxyuridine 5′-monophosphate disodium salt Sigma Grade

Sigma-Aldrich

D3876

2′-Deoxyuridine 5′-monophosphate disodium salt

2′-Deoxyuridine 5′-triphosphate sodium salt ≥95%

Sigma-Aldrich

D4001

2′-Deoxyuridine 5′-triphosphate sodium salt

2′-Deoxycytidine 5′-monophosphate sodium salt Sigma Grade, ≥98%

Sigma-Aldrich

D7625

2′-Deoxycytidine 5′-monophosphate sodium salt

Uridine 5′-monophosphate disodium salt ≥99%

Sigma-Aldrich

U6375

Uridine 5′-monophosphate disodium salt

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

microbial (fermentation)

biological source

(chemical)

grade

Sigma Grade

grade

-

grade

Sigma Grade

grade

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥95%

assay

≥98%

assay

≥99%

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) is a substrate for thymidylate synthase and is converted to deoxythymidine monophosphate (dTMP).[1]

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[1]
  • to stimulate proliferation of peripheral blood mononuclear cell (PBMCs) exposed to influenza virus antigen
  • in thymidylate synthase activity assay Helicobacter pylori[2]

Biochem/physiol Actions

2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) conversion to pyrimidine is inhibited by methotrexate.[1] The inhibition of dUMP to deoxythymidine monophosphate (dTMP) at the methylation step is a key in controlling bacterial and eukaryotic cell growth.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000522299
0000522299
0000474518
0000474518
0000411514

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Adam Jarmuła et al.
Bioorganic & medicinal chemistry, 15(6), 2346-2358 (2007-02-06)
Thymidylate synthase (TS) is a target enzyme for a number of anticancer agents including the 5-fluorouracil metabolite, FdUMP. The present paper reports on molecular modeling studies of the effect of substitution at C(5) position in the pyrimidine ring of the
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
Eric M Koehn et al.
Nature, 458(7240), 919-923 (2009-04-17)
Biosynthesis of the DNA base thymine depends on activity of the enzyme thymidylate synthase to catalyse the methylation of the uracil moiety of 2'-deoxyuridine-5'-monophosphate. All known thymidylate synthases rely on an active site residue of the enzyme to activate 2'-deoxyuridine-5'-monophosphate.
Biochemistry: Anchors away.
Maria Paola Costi et al.
Nature, 458(7240), 840-841 (2009-04-17)
Aldo A Arvizu-Flores et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 150(3), 406-413 (2009-06-30)
Thymidylate synthase (TS) catalyzes the synthesis of deoxythymidine monophosphate (dTMP), which is an essential precursor for DNA synthesis. The rationale underlying drug design is to identify compounds that differentially inhibit a viral or parasite enzyme vs. the host homologue. We
View All Related Papers

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