2'-Deoxycytidine

Base Information

• Chemical Name: 2'-Deoxycytidine
• CAS No.: 951-77-9
• Deprecated CAS: 1236362-96-1
• Molecular Formula: C9H13N3O4
• Molecular Weight: 227.22
• Hs Code.: PRICE
• European Community (EC) Number: 213-454-1
• UNII: 0W860991D6
• DSSTox Substance ID: DTXSID70883620
• Nikkaji Number: J14.406A
• Wikipedia: Deoxycytidine
• Wikidata: Q422504
• NCI Thesaurus Code: C420
• Metabolomics Workbench ID: 37025
• ChEMBL ID: CHEMBL66115
• Mol file: 951-77-9.mol

Synonyms:Cytosine Deoxyribonucleoside;Cytosine Deoxyriboside;Deoxycytidine;Deoxyribonucleoside, Cytosine;Deoxyriboside, Cytosine

Chemical Property of 2'-Deoxycytidine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 209-211 °C(lit.)
• Refractive Index: 59 ° (C=1, H2O)
• Boiling Point: 497.625 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 254.754 °C
• PSA: 119.83000
• Density: 1.733 g/cm³
• LogP: -1.01690
• Storage Temp.: Store at RT.
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in water, DMSO.
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 227.09060590
• Heavy Atom Count: 16
• Complexity: 355

Purity/Quality:

98% ^*data from raw suppliers

2’-DeoxyCytidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1C(C(OC1N2C=CC(=NC2=O)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O
• Recent ClinicalTrials: Phase II Study of DC Versus 5-FU/CF as Chemotherapy and Concurrent Chemoradiotherapy for Locally Advanced Gastric Cancer
• Recent EU Clinical Trials: Prophylactic vaccination with autologous dendritic cells against human cytomegalovirus: a pilot study in patients awaiting kidney transplantation
• Description: 2'-Deoxycytidine is a deoxyribonucleotide that is used in the synthesis of DNA. 2'-Deoxycytidine has been shown to inhibit the kinase activity of IL-2 receptor and Toll-like receptor, which are proteins that regulate the immune response. 2'-Deoxycytidine also inhibits DNA polymerase activity and thermal expansion, which may make it a good candidate as an anticancer drug.
• Uses: 2?-Deoxycytidine (deoxyC) is one of the deoxynucleosides which after phosphorylation to dCTP is used to synthesis DNA via various DNA polymerases or reverse transcriptases. 2?-Deoxycytidine (deoxyC) is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2?-deoxyuridine. 2?-Deoxycytidine is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK).

Technology Process of 2'-Deoxycytidine

There total 125 articles about 2'-Deoxycytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

{5'-d(ATGGGC[15N3,13C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCGCCGTACAAG)-5'} → 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one (137608-88-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + 2'-deoxyadenosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

{5'-d(ATGGGC[¹⁵N_3,¹³_C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCGCCGTACAAG)-5'}; With oxygen; sodium chloride; riboflavin; In aq. buffer; for 0.333333h; pH=7; Irradiation;

With nuclease P₁; deferoxamine; ammonium acetate; zinc(II) chloride; alkaline phosphatase; In aq. buffer; at 37 ℃; for 2h; pH=5.3; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/ja411636j

Reference yield:

{5'-d(ATGGG(5-methyl-C)[15N3,13C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCGCCGTACAAG)-5'} → 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one (137608-88-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + 2'-deoxyadenosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

{5'-d(ATGGG(5-methyl-C)[¹⁵N_3,¹³_C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCGCCGTACAAG)-5'}; With oxygen; sodium chloride; riboflavin; In aq. buffer; for 0.333333h; pH=7; Irradiation;

With nuclease P₁; deferoxamine; ammonium acetate; zinc(II) chloride; alkaline phosphatase; In aq. buffer; at 37 ℃; for 2h; pH=5.3; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/ja411636j

Reference yield:

{5'-d(ATGGGC[15N3,13C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCG(5-methyl-C)CGTACAAG)-5'} → 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one (137608-88-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + 2'-deoxyadenosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

{5'-d(ATGGGC[¹⁵N_3,¹³_C1-2'-G]GCATGAAC)-3'}*{3'-d(TACCCG(5-methyl-C)CGTACAAG)-5'}; With oxygen; sodium chloride; riboflavin; In aq. buffer; for 0.333333h; pH=7; Irradiation;

With nuclease P₁; deferoxamine; ammonium acetate; zinc(II) chloride; alkaline phosphatase; In aq. buffer; at 37 ℃; for 2h; pH=5.3; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/ja411636j

upstream raw materials:

N⁴-acetyl-O^3'_,O5'-bis-(4-chloro-benzoyl)-2'-deoxy-cytidine

3',5'-di-O-benzoyl-2'-deoxycytidine

2'-deoxycytidine monohydrochloride

2'-Deoxyguanosine

Downstream raw materials:

2'-Deoxyguanosine

4-methylamino-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one

[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-(4-iodo-phenyl)-amine

C₃₆H₄₀N₆O₇

Refernces

• 1、 Peng, Haihui,Jie, Jialong,Mortimer, Ifor P.,Ma, Zehan,Su, Hongmei,Greenberg, Marc M.. "Reactivity and DNA Damage by Independently Generated 2′-Deoxycytidin-N4-yl Radical". . p. 14738 - 14747. Retrieved 2021/09/18.
• 2、 Xie, Li-Jun,Yang, Xiao-Ti,Wang, Rui-Li,Cheng, Hou-Ping,Li, Zhi-Yan,Liu, Li,Mao, Lanqun,Wang, Ming,Cheng, Liang. "Identification of Flavin Mononucleotide as a Cell-Active Artificial N6-Methyladenosine RNA Demethylase". supporting information. p. 5028 - 5032. Retrieved 2019/03/17.