2'-Deoxyuridine 5'-monophosphate disodium salt Chemical Properties

storage temp. 

-20°C

solubility 

PBS (pH 7.2): 1 mg/ml

form 

Powder

color 

White to Off-white

biological source

synthetic (organic)

Water Solubility 

Soluble in water.

InChI

InChI=1/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);;/t5-,6+,8+;;/s3

InChIKey

WXIVKKBDJOCRNB-BAJMBWAYNA-N

SMILES

O=C1NC(=O)C=CN1[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1.[NaH] |&1:8,10,12,r|

CAS DataBase Reference

42155-08-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29349990

Storage Class

11 - Combustible Solids

Hazard Classifications

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

MSDS

• Language:English Provider:SigmaAldrich

2'-Deoxyuridine 5'-monophosphate disodium salt Usage And Synthesis

Description

2'-Deoxyuridine 5'-monophosphate disodium salt is a nucleoside analog that inhibits the synthesis of DNA and RNA by inhibiting the enzyme thymidylate synthase, which prevents the formation of dTMP from deoxyuridine 5'-triphosphate. 2'-Deoxyuridine 5'-monophosphate disodium salt has been shown to be effective in treating squamous cell cancer and hyperproliferative diseases such as chronic myelogenous leukemia. 2'-Deoxyuridine 5'-monophosphate disodium salt is also used as an antiviral agent against HIV, herpes simplex virus, and varicella zoster virus.

Uses

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.

General Description

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

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.

Synthesis

2'-iodouridine (5g, 14.1mmol), 10% wet palladium carbon (0.1g) and triethylamine (1.8g, 18mmol), was added to ethanol (100mL), stirred at room temperature for 30min, displacing hydrogen, maintaining hydrogen pressure in the reaction flask 1atm, stirred at room temperature for 2h, TLC showed that the reaction of the raw materials was complete, added 2g Diatomaceous earth, stirred for 10min, filtration to remove palladium carbon, filtrate concentration to get oil, and then add phosphoric acid (50mL), heating to dissolve, after cooling there is a white solid precipitation, filtration, washed to almost colorless, filter cake drying to get the crude 2'-deoxyuridine-5'-disodium monophosphate, recrystallization and filtration, drying, to get the pure product 2.96 g The product was dried and recrystallized to obtain 2.96g of pure product with 92% yield and 98% purity by HPLC.

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