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Merck
CN

D7750

2′-Deoxycytidine 5′-monophosphate

≥95.0%, synthetic, powder

Synonym(s):

Deoxycytidylic acid, dCMP

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About This Item

Empirical Formula (Hill Notation):
C9H14N3O7P
CAS Number:
1032-65-1
Molecular Weight:
307.20
NACRES:
NA.51
PubChem Substance ID:
24894158
UNSPSC Code:
41106305
EC Number:
213-849-9
MDL number:
MFCD00006546
Beilstein/REAXYS Number:
41062
Assay:
≥95.0%
Biological source:
synthetic
Form:
powder
Solubility:
1 M NH4OH: 50 mg/mL, clear, colorless
Storage temp.:
−20°C

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Product Name

2′-Deoxycytidine 5′-monophosphate, Sigma Grade, ≥95.0%

InChI key

NCMVOABPESMRCP-SHYZEUOFSA-N

InChI

1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1

SMILES string

NC1=NC(=O)N(C=C1)[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2

biological source

synthetic

grade

Sigma Grade

assay

≥95.0%

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

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Application

2′-Deoxycytidine 5′-monophosphate (dCMP) 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 biosynthesis.
2′-Deoxycytidine 5′-monophosphate has been used in Raman spectroscopic studies to determine its Raman total half bandwidths.

General description

2′-Deoxycytidine 5′-monophosphate is a deoxynucleotide building block via which DNA is made. It consists of a 2′-deoxy-β-D-ribofuranose, linked through an N-β-D-glycosidic linkage to a heterocycle nitrogen cytosine. It is phosphorylated at carbon C-5′.

flash_point_f

Not applicable

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000522633
0000522633
0000495424
0000495424
SLCP6879

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Essentials of Chemical biology (2013)
Zimin Liu et al.
American journal of translational research, 8(11), 4764-4777 (2016-12-03)
microRNAs (miRs) are small noncoding RNAs that modulate a variety of cellular processes by regulating multiple targets, which can promote or inhibit the development of malignant behaviors. Accumulating evidence suggests that microRNA-221 (miR-221) plays important roles in human carcinogenesis. It
Páraic M Keane et al.
Journal of the American Chemical Society, 133(12), 4212-4215 (2011-03-10)
The role of N1-substitution in controlling the deactivation processes in photoexcited cytosine derivatives has been explored using picosecond time-resolved IR spectroscopy. The simplest N1-substituted derivative, 1-methylcytosine, exhibits relaxation dynamics similar to the cytosine nucleobase and distinct from the biologically relevant
Dimitri Topalis et al.
Journal of medicinal chemistry, 54(1), 222-232 (2010-12-07)
Acyclic nucleoside phosphonates (ANPs) are at the cornerstone of DNA virus and retrovirus therapies. They reach their target, the viral DNA polymerase, after two phosphorylation steps catalyzed by cellular kinases. New pyrimidine ANPs have been synthesized with unsaturated acyclic side
Ivan Zlatev et al.
Bioorganic & medicinal chemistry, 17(19), 7008-7014 (2009-09-01)
The replacement of the pyrophosphate moiety of 2'-deoxynucleoside triphosphates by non natural delta-dicarboxylic butyl amino acid allows incorporation of natural 2'-deoxycytidine into DNA using HIV-1 reverse transcriptase (RT) as enzyme. In contrast, the 3'-deoxycytidine analogue was not a substrate of
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