Deoxycytidine
Structural formula | ||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | ||||||||||||||||||||||
Surname | Deoxycytidine | |||||||||||||||||||||
other names |
|
|||||||||||||||||||||
Molecular formula | C 9 H 13 N 3 O 4 | |||||||||||||||||||||
Brief description |
colorless to pale yellow crystalline powder |
|||||||||||||||||||||
External identifiers / databases | ||||||||||||||||||||||
|
||||||||||||||||||||||
properties | ||||||||||||||||||||||
Molar mass | 227.22 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
|||||||||||||||||||||
Melting point |
209-211 ° C |
|||||||||||||||||||||
solubility |
50 mg / ml water |
|||||||||||||||||||||
safety instructions | ||||||||||||||||||||||
|
||||||||||||||||||||||
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 .
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.