Cytidine 5’-monophosphate Chemical Properties

Melting point:

~222 °C (dec.)

Boiling point:

678.1±65.0 °C(Predicted)

Density 

2.15±0.1 g/cm3(Predicted)

refractive index 

9.8 ° (C=1, 0.5mol/L Na2HPO4)

storage temp. 

2-8°C

solubility 

Water (Slightly, Heated)

pka

pK2:4.39(0);pK3:6.62(+1) (25°C)

form 

crystalline

color 

White

Water Solubility 

soluble

BRN 

46982

InChI

InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

InChIKey

IERHLVCPSMICTF-JDNPWWSISA-N

SMILES

P(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)(O)(O)=O

CAS DataBase Reference

63-37-6(CAS DataBase Reference)

EPA Substance Registry System

5'-Cytidylic acid (63-37-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-37/39-36-26

WGK Germany 

3

RTECS 

HA3980000

F 

10-21

HS Code 

29349990

Toxicity

LD50 intraperitoneal in mouse: > 1gm/kg

MSDS

• Language:English Provider:CMP
• Language:English Provider:SigmaAldrich

Cytidine 5’-monophosphate Usage And Synthesis

Description

Cytidine 5'-monophosphate, also known as 5'-CMP, is a nucleotide that is used as a monomer in RNA. 5'-CMP is a key intermediate in the preparation of several nucleotide derivatives and is widely used in food and pharmaceutical industries.

Chemical Properties

white crystalline powder

Uses

A constituent of nucleic acids. It was isolated from yeast nucleic acid.

Uses

Cytidine 5′-monophosphate has been used in Raman spectroscopy studies.

Definition

ChEBI: A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.

Production Methods

As a key intermediate in preparing several nucleotide derivatives, cytidine 5′-monophosphate (5′-CMP) is widely applied in food and pharmaceutical industries. Enzymatic synthesis of 5′-CMP is catalyzed by cytidine kinase (CK, EC 2.7.1.213), a type of nucleoside kinase that belongs to the PfkB family. Li et al. constructed a highly efficient biosynthesis system for manufacturing 5′-CMP in vitro. CK was used for the biotransformation of cytidine to 5′-CMP, while polyphosphate kinase (PPK) was coupled for adenosine triphosphate regeneration. Both CK and PPK were selected from extremophiles, possessing great potential for biocatalytic synthesis. After optimization, 96 mM 5′-CMP was produced within 6 h, and the yield reached nearly 100%[1].

Biochem/physiol Actions

Cytidine 5′-monophosphate (CMP) is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form CDP which upon phosphorylation to CTP supports DNA and RNA biosynthesis.

References

[1] Zonglin Li. “Efficient One-Pot Synthesis of Cytidine 5′-Monophosphate Using an Extremophilic Enzyme Cascade System.” Journal of Agricultural and Food Chemistry 68 34 (2020): 9188–9194.

Cytidine 5’-monophosphate(63-37-6)Related Product Information

• Polyinosinic acid-polycytidylic acid
• Tributyl phosphate
• L-DIHYDROOROTIC ACID
• NUCLEOSIDE PHOSPHORYLASE BACTERIAL
• Cytosine
• Ethyl 2-(Chlorosulfonyl)acetate
• Tylosin phosphate
• Triethyl phosphate
• Fluorocytosine
• Ribavirin
• AMPHISOL A
• Hyaluronic acid
• Citric acid
• 5-Fluorocytidine
• 5-Azacytidine
• Trisodium phosphate
• Folic acid
• Cytidine-5'-triphosphate disodium salt dihydrate