951-78-0 Usage
Description
Different sources of media describe the Description of 951-78-0 differently. You can refer to the following data:
1. 2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used
to prepare combined deoxynucleoside drugs or used as chemical reagents
for biochemical research. At the same time, it can be used as an
intermediate to synthesize some antiviral nucleoside drugs and molecular
markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine.
2. 2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. 2'-Deoxyuridine has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. 2'-Deoxyuridine is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
Physical properties
2'-Deoxyuridine is a white or off-white powdered solid with a melting
point of 167 to 169 °C. Its boiling point is roughly estimated to be
370.01°C. It is slightly soluble in water, DMSO, and slightly soluble in
methanol when heated.
synthesis
The precursor 3,5-(toluoyl)-2-deoxy-(N1,N3-15N)-uridine
(1) was synthesized according to Schiesser et al.4 In a round bottom
flask 1 (76 mg, 0.16 mmol, 1.0 eq.) was dissolved in dry MeOH (2.1 mL)
and K2CO3 (49 mg, 0.35 mmol, 2.2 eq.) was added.
The suspension was stirred at 40 °C for 6 h. The solvent was removed by
rotary evaporation. The residue was then suspended in H2O (5 mL) and extracted with DCM (5 mL). The aqueous layer was then concentrated to dryness, redissolved in H2O and subjected to RP-HPLC (0% to 20% MeCN in water in 45 min, 5 mL/min). [15N2]-dU as a white solid (31 mg, 0.13 mmol, 84%).
Chemical Properties
White crystalline powder
Uses
Different sources of media describe the Uses of 951-78-0 differently. You can refer to the following data:
1. 2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.
2. 2′-Deoxyuridine (dU) is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2′-Deoxyuridines used as labeling substrates include chloro-2′-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2′-deoxyuridine include 5-ethynyl-2′-deoxyuridine (DdU) and 5-hydroxymethyl-2′-deoxyuridine (HmdU).
3. An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease
Biological Activity
2'-deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of dna synthesis and degradation mechanisms.
Check Digit Verification of cas no
The CAS Registry Mumber 951-78-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,5 and 1 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 951-78:
(5*9)+(4*5)+(3*1)+(2*7)+(1*8)=90
90 % 10 = 0
So 951-78-0 is a valid CAS Registry Number.
951-78-0Relevant articles and documents
An Engineered Cytidine Deaminase for Biocatalytic Production of a Key Intermediate of the Covid-19 Antiviral Molnupiravir
Birmingham, William R.,Burke, Ashleigh J.,Charnock, Simon J.,Crawshaw, Rebecca,Finnigan, James D.,Green, Anthony P.,Holgate, Gregory M.,Lovelock, Sarah L.,Muldowney, Mark P.,Rowles, Ian,Thorpe, Thomas W.,Turner, Nicholas J.,Young, Carl,Zhuo, Ying,Zucoloto Da Costa, Bruna
supporting information, p. 3761 - 3765 (2022/03/15)
The Covid-19 pandemic highlights the urgent need for cost-effective processes to rapidly manufacture antiviral drugs at scale. Here we report a concise biocatalytic process for Molnupiravir, a nucleoside analogue recently approved as an orally available treatment for SARS-CoV-2. Key to the success of this process was the development of an efficient biocatalyst for the production of N-hydroxy-cytidine through evolutionary adaption of the hydrolytic enzyme cytidine deaminase. This engineered biocatalyst performs >85 000 turnovers in less than 3 h, operates at 180 g/L substrate loading, and benefits from in situ crystallization of the N-hydroxy-cytidine product (85% yield), which can be converted to Molnupiravir by a selective 5′-acylation using Novozym 435.
Thermodynamic Reaction Control of Nucleoside Phosphorolysis
Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias
supporting information, p. 867 - 876 (2020/01/24)
Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).
Novel Use
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Paragraph 0020, (2019/05/24)
The invention relates to the use of an amine masked moiety in a method of enzymatic nucleic acid synthesis. The invention also relates to said amine masked moieties per se and a process for preparing nucleotide triphosphates comprising said amine masked moieties.
