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Merck

D7750

Sigma-Aldrich

2′-Deoxycytidine 5′-monophosphate

Sigma Grade, ≥95.0%

Sinónimos:

Deoxycytidylic acid, dCMP

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About This Item

Fórmula empírica (notación de Hill):
C9H14N3O7P
Número de CAS:
Peso molecular:
307.20
Beilstein/REAXYS Number:
41062
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

grade

Sigma Grade

assay

≥95.0%

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

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

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

InChI key

NCMVOABPESMRCP-SHYZEUOFSA-N

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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′.

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.

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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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
Susan Quinn et al.
Chemical communications (Cambridge, England), (21)(21), 2130-2132 (2007-05-24)
A strong infrared band at 1574 cm(-1) is observed following 267 nm excitation of 2'-deoxycytidine (tau = 37 +/- 4 ps) or 2'-deoxycytidine 5'-monophosphate (tau = 33 +/- 4 ps); this band is provisionally attributed to an 1n(N)pi* state and
Makusu Tsutsui et al.
Journal of the American Chemical Society, 133(23), 9124-9128 (2011-05-13)
We report label-free electrical detections of chemically modified nucleobases in a DNA using a nucleotide-sized electrode gap. We found that methyl substitution contributes to increase the tunneling conductance of deoxycytidines, which was attributed to a shift of the highest occupied
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
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

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