Deoxycytidine 5'-monophosphate

Base Information

• Chemical Name: Deoxycytidine 5'-monophosphate
• CAS No.: 1032-65-1
• Molecular Formula: C9H14N3O7P
• Molecular Weight: 307.2
• Hs Code.: 29349990
• European Community (EC) Number: 235-995-2,213-849-9
• UNII: W7A9174XQL
• DSSTox Substance ID: DTXSID20908251
• Nikkaji Number: J14.407J
• Wikipedia: Deoxycytidine_monophosphate
• Wikidata: Q2742455
• Metabolomics Workbench ID: 37660
• ChEMBL ID: CHEMBL374699
• Mol file: 1032-65-1.mol

Synonyms:Acid, Deoxycytidylic;Acids, Deoxycytidylic;DCMP;Deoxycytidine Monophosphate;Deoxycytidylic Acid;Deoxycytidylic Acids;Monophosphate, Deoxycytidine

Chemical Property of Deoxycytidine 5'-monophosphate

Chemical Property:

• Appearance/Colour: White fine crystals
• Melting Point: 169-172 °C (dec.)
• Refractive Index: 37 ° (C=1, H2O)
• Boiling Point: 633.8 °C at 760 mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: 337.1 °C
• PSA: 166.94000
• Density: 2.01 g/cm³
• LogP: -0.83560
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL, clear, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 307.05693679
• Heavy Atom Count: 20
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

2'-Deoxycytidine 5'-Monophosphate Hydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=NC2=O)N)COP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)COP(=O)(O)O)O
• Uses: A phosphorylated metabolite of the deoxyribonucleoside 2’Deoxycytidine. A constituent of Deoxyribonucleic acid. Studies show that it increases influenza virus antigen-induced immune cell proliferatio n. 2'-Deoxycytidine-5'-monophosphate is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form dCDP which upon phosphorylation to dCTP supports DNA and RNA biosynthesis.

Technology Process of Deoxycytidine 5'-monophosphate

There total 27 articles about Deoxycytidine 5'-monophosphate 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: 87.0%

2'-Deoxycytidine (951-77-9) → cytidine 5'-(dihydrogen phosphate) (1032-65-1,25609-92-1)

Guidance literature:

2'-Deoxycytidine; With trichlorophosphate; at 20 ℃; for 0.15h; Flow reactor; Green chemistry;

With water; at 20 ℃; Temperature; chemoselective reaction; Flow reactor; Green chemistry;

DOI:10.1021/op5002066

Reference yield: 51.0%

C34H47N10O23P3 → cytidine 5'-(dihydrogen phosphate) (1032-65-1,25609-92-1) + C25H35N7O17P2 + C25H35N7O16P2

Guidance literature:

With Tris-borate buffer; at 90 ℃; for 7h;

DOI:10.1021/ja00081a007

Reference yield:

5'-d(CAGCTPMeG), PMe = methylphosphonate link → 5'-d(pTPMeG), PMe = methylphosphonate link + cytidine 5'-(dihydrogen phosphate) (1032-65-1,25609-92-1) + 2'-deoxyadenosine-5'-monophosphoric acid (653-63-4) + 2'-deoxyguanosine 5'-monophosphate (902-04-5) + 2'-Deoxycytidine (951-77-9)

Guidance literature:

With nuclease P₁ from Penicillium citrinum; at 37 ℃; for 0.0833333h; pH=5.4; Enzymatic reaction;

DOI:10.1021/tx300319y

upstream raw materials:

C₅₄H₇₂N₁₈O₃₆P₆

C₆₃H₈₄N₂₁O₄₂P₇

2'-deoxycytidine 3',5-cyclic monophosphate

2'-deoxyguanosine 5'-monophosphate

Downstream raw materials:

(S)-3,5-dihydroxy-4-oxo-pentanal

2-deoxy-D-ribose 5-phosphate, free acid

Cytosine

2,5-dideoxy-pentos-3,4-diulose

Refernces

• 1、 Eckstein. "Oligodesoxynucleotides with terminal 5'-phosphate groups". . p. 2236 - 2241. Retrieved 1967.
• 2、 Nair, Vasu,Pal, Suresh. "Resistance towards exonucleases of dinucleotides with stereochemically altered internucleotide phosphate bonds". . p. 289 - 291. Retrieved 2004.
• 3、 Al-Madhoun, Ashraf Said,Eriksson, Staffan,Wang, Zhi-Xian,Naimi, Ebrahim,Knaus, Edward E.,Wiebe, Leonard I.. "Phosphorylation of isocarbostyril- and difluorophenyl-nucleoside thymidine mimics by the human deoxynucleoside kinases". . p. 1865 - 1874. Retrieved 2004.
• 4、 Johansson, Magnus,Karlsson, Anna. "Differences in kinetic properties of pure recombinant human and mouse deoxycytidine kinase". . p. 163 - 168. Retrieved 1995.
• 5、 Serra, Immacolata,Conti, Silvia,Piskur, Jure,Clausen, Anders R.,Munch-Petersen, Birgitte,Terreni, Marco,Ubiali, Daniela. "Immobilized Drosophila melanogaster deoxyribonucleoside kinase (DmdNK) as a high performing biocatalyst for the synthesis of purine arabinonucleotides". . p. 563 - 570. Retrieved 2014.
• 6、 Wang, Danyang,Zhang, Yu,Kleiner, Ralph E.. "Cell- And Polymerase-Selective Metabolic Labeling of Cellular RNA with 2′-Azidocytidine". . p. 14417 - 14421. Retrieved 2020.
• 7、 Zhu, Chenjie,Tang, Chenglun,Cao, Zhi,He, Wei,Chen, Yong,Chen, Xiaochun,Guo, Kai,Ying, Hanjie. "Fully automated continuous meso-flow synthesis of 5′-nucleotides and deoxynucleotides". . p. 1575 - 1581. Retrieved 2015/02/19.