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C1131

Sigma-Aldrich

Cytidine 5′-monophosphate

Sigma Grade, ≥99% (HPLC), synthetic, powder

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Synonym(s):
5′-CMP, 5′-Cytidylic acid, C-5′-P
Empirical Formula (Hill Notation):
C9H14N3O8P
CAS Number:
Molecular Weight:
323.20
Beilstein/REAXYS Number:
46982
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

Quality Level

grade

Sigma Grade

assay

≥99% (HPLC)

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O

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

InChI key

IERHLVCPSMICTF-XVFCMESISA-N

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This Item
C1006C9630A9501
Cytidine 5′-monophosphate Sigma Grade, ≥99% (HPLC), synthetic, powder

C1131

Cytidine 5′-monophosphate

grade

Sigma Grade

grade

Sigma Grade

grade

-

grade

-

form

powder

form

crystalline

form

powder

form

powder

assay

≥99% (HPLC)

assay

≥99%

assay

≥95% (HPLC)

assay

≥98.5% (HPLC)

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

solubility

water: 100 mg/mL, clear to very slightly hazy, colorless to very faintly yellow

solubility

water: 50 mg/mL, clear, colorless

solubility

H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

Application

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

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.
The nucleoside diphosphates cytidine diphosphate (CDP) and uridine diphosphate (UDP) are essential for pyrimidine synthesis Cytidine 5′-monophosphate (CMP) nucleotide is useful in adsorption studies on biomimetic apatite for mimicking bone mineral. It also serves an immunity supplement in pediatric formulas.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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A Hirono et al.
Clinica chimica acta; international journal of clinical chemistry, 130(2), 189-197 (1983-05-30)
Three new variants of pyrimidine 5'-nucleotidase (P5N) found in Japan were studied. They are characterized by slow electrophoretic mobility and a high Michaelis constant for cytidine 5'-monophosphate as has been described in previously reported cases, but are unique with respect
Linda J Reha-Krantz et al.
Biochemistry, 50(46), 10136-10149 (2011-10-26)
The adenine base analogue 2-aminopurine (2AP) is a potent base substitution mutagen in prokaryotes because of its enhanceed ability to form a mutagenic base pair with an incoming dCTP. Despite more than 50 years of research, the structure of the
Ho Jun Lee et al.
The Journal of biological chemistry, 286(41), 35922-35932 (2011-08-13)
Sialic acids play important roles in various biological processes and typically terminate the oligosaccharide chains on the cell surfaces of a wide range of organisms, including mammals and bacteria. Their attachment is catalyzed by a set of sialyltransferases with defined
Haifeng C Xu et al.
Journal of virology, 89(9), 4748-4759 (2015-02-13)
The B cell-activating factor (BAFF) is critical for B cell development and humoral immunity in mice and humans. While the role of BAFF in B cells has been widely described, its role in innate immunity remains unknown. Using BAFF receptor
Sarah Schott et al.
International journal of cancer, 131(9), 2165-2174 (2012-02-11)
Melanoma is an increasingly common and potentially fatal malignancy of the skin and some mucous membranes. As no cure exists for metastatic disease, there is an urgent need for novel drugs. 2'-Deoxy-5-fluorouridylyl-(3'-5')-3'-C-ethynylcytidine [5-FdU(3'-5')ECyd] and 3'-C-ethynylcytidinylyl-(5' → 1-O)-2-O-octadecyl-sn-glycerylyl-(3-O → 5')-2'-deoxy-5-fluorouridine [ECyd-lipid-5-FdU]

Protocols

ZIC®-cHILIC is a densely bonded zwitterionic stationary phase with phosphorylcholine functional groups covalently attached to silica.

HILIC separation is an alternative that permits sensitive MS detection and without the use of ion-pair reagents.

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