Deoxycytidine

Structural formula
General
Surname	Deoxycytidine
other names	dC, CdR or dCyd (short code); 2'-deoxycytidine; 1-β- D -deoxyribofuranosylcytosine; 1 - [(2 R , 4 S , 5 R ) -4-hydroxy-5- (hydroxymethyl) oxolan-2-yl] -4-aminopyrimidin-2-one; DEOXYCYTIDINE ( INCI ) ;
Molecular formula	C 9 H 13 N 3 O 4
Brief description	colorless to pale yellow crystalline powder
External identifiers / databases
EC number	213-454-1
ECHA InfoCard	100.012.231
PubChem	13711
ChemSpider	13117
DrugBank	DB02594
Wikidata	Q422504
properties
Molar mass	227.22 g mol −1
Physical state	firmly
Melting point	209-211 ° C
solubility	50 mg / ml water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Deoxycytidine ( dC for short or just C in DNA sequences ) is a nucleoside and consists of the nucleosine base cytosine and the sugar β- D -deoxyribose .

Deoxycytidine is part of deoxyribonucleic acid (DNA) and forms a base pair there with deoxyguanosine . The analog with ribose is cytidine .

Structural formula of a GC base pair

Depending on the number of phosphate residues , it forms the basis for the nucleotides deoxycytidine monophosphate (dCMP), deoxycytidine diphosphate (dCDP) or deoxycytidine triphosphate (dCTP).

Under physiological conditions, a small part of the deoxycytidine contained in the DNA dehydrates to deoxyuridine , for which special repair systems exist in the cells. When 5-methyldeoxycytidine is deaminated , however, the deoxythymidine , which is also normally contained in the DNA, is produced , which cannot be recognized as faulty, which means that it can pair with deoxyadenosine in the next round of replication , which then results in a transition from deoxycytidine to deoxythymidine and on the opposite DNA strand from deoxyguanosine to deoxyadenosine.

Derivatives

Decitabine (aza derivative)
Gemcitabine (2 ', 2'-difluorodeoxycytidine)

Individual evidence

↑ Entry on DEOXYCYTIDINE in the CosIng database of the EU Commission, accessed on March 31, 2020.
↑ ^a ^b ^c ^d data sheet 2'-Deoxycytidine from Sigma-Aldrich , accessed on January 22, 2012 ( PDF ).
↑ 2'-Deoxycytidine data sheet from Acros, accessed on February 22, 2011.
↑ Ralph Remus: Distribution of the fifth DNA base 5-methyl-deoxycytidine in the mammalian genome: DNA methylation patterns of endogenous retroviral sequences of the Syrian hamster (Mesocricetus auratus) and in the promoters of human erythrocyte membrane skeleton proteins (Homo sapiens) , dissertation, University of Cologne, 2000.

[CosIng-1] Entry on DEOXYCYTIDINE in the CosIng database of the EU Commission, accessed on March 31, 2020.

[Sigma-2] ta sheet 2'-Deoxycytidine from Sigma-Aldrich , accessed on January 22, 2012 ( PDF ).

[Acros-3] 2'-Deoxycytidine data sheet from Acros, accessed on February 22, 2011.

[4] Ralph Remus: Distribution of the fifth DNA base 5-methyl-deoxycytidine in the mammalian genome: DNA methylation patterns of endogenous retroviral sequences of the Syrian hamster (Mesocricetus auratus) and in the promoters of human erythrocyte membrane skeleton proteins (Homo sapiens) , dissertation, University of Cologne, 2000.