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D7750

Sigma-Aldrich

2′-Deoxycytidine 5′-monophosphate

Sigma Grade, ≥95.0%

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
Beilstein:
41062
EC Number:
213-849-9
MDL number:
MFCD00006546
UNSPSC Code:
41106305
PubChem Substance ID:
24894158
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Montserrat Terrazas et al.
Chemistry & biodiversity, 5(1), 31-39 (2008-01-22)
The replacement of the pyrophosphate moiety of deoxynucleoside triphosphates by L-aspartic acid allows incorporation of natural deoxynucleosides into DNA using HIV reverse transcriptase (RT) as enzyme, while retaining the canonical base-pair selectivity. N-Methylation of the L-aspartic acid leaving group results
Frédéric A Perras et al.
Physical chemistry chemical physics : PCCP, 14(14), 4677-4681 (2012-03-06)
Obtaining definitive information concerning the coordination environment of sodium ions which balance the negative charges found in nucleotides is a challenging task. We show that high resolution 1D and 2D (23)Na NMR spectra of sodium nucleotides obtained in the solid
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
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
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
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