Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15N3O4 |
| Molecular Weight | 241.2438 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N=C1N
InChI
InChIKey=LUCHPKXVUGJYGU-XLPZGREQSA-N
InChI=1S/C10H15N3O4/c1-5-3-13(10(16)12-9(5)11)8-2-6(15)7(4-14)17-8/h3,6-8,14-15H,2,4H2,1H3,(H2,11,12,16)/t6-,7+,8+/m0/s1
| Molecular Formula | C10H15N3O4 |
| Molecular Weight | 241.2438 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
In mammalian as well as in plant DNA, and in the DNA of many other organisms, there occurs a fifth nucleotide, 5-methyldeoxycytidine (5-mC), in addition to the traditionally recognized four nucleotides A, C, G, and T. The modification of cytidine to 5-mC, apparently the only one among the nucleotides in mammalian DNA, is introduced postreplicationally by several DNA methyltransferases (DNMT) which are chosen depending on the functional context of their enzymatic activity: DNA can be methylated de novo, still a most enigmatic series of events, or a given pattern of DNA methylation in the genome can be maintained upon replication. In general, 5-mC can be considered as a modulator of protein-DNA interactions and genome activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Generation of AcGFP fusion with single-chain Fv selected from a phage display library constructed from mice hyperimmunized against 5-methyl 2'-deoxycytidine. | 2010-11 |
|
| High-performance capillary electrophoretic method for the quantification of global DNA methylation: application to methotrexate-resistant cells. | 2009-04-01 |
|
| Quantification of global DNA methylation by capillary electrophoresis and mass spectrometry. | 2009 |
|
| A high-throughput and sensitive method to measure global DNA methylation: application in lung cancer. | 2008-08-03 |
|
| Reactions of {4-[bis(2-chloroethyl)amino]phenyl}acetic acid (phenylacetic acid mustard) with 2'-deoxyribonucleosides. | 2007-03 |
|
| Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2'-deoxycytidine, 2'-deoxy-5-methylcytidine, and thymidine. | 2004-03 |
|
| Nucleosides and nucleotides. Part 214: thermal stability of triplexes containing 4'alpha-C-aminoalkyl-2'-deoxynucleosides. | 2002-09 |
|
| High-performance capillary electrophoretic method for the quantification of 5-methyl 2'-deoxycytidine in genomic DNA: application to plant, animal and human cancer tissues. | 2002-06 |
|
| Development of new amination reaction at 4-position of pyrimidine nucleosides. | 2002 |
Patents
Sample Use Guides
Electroporation of Chinese hamster V-79 cells in the presence of millimolar concentrations of 5-methyl-2'-deoxycytidine 5'-triphosphate (5mdCTP) led to high-level direct incorporation of this nucleotide into DNA polymer. Under optimum conditions, approximately 2 x 10(8) molecules of 5 mdCTP were calculated to have been incorporated into each unit genome (6 pg of DNA). Since a diploid mammalian genome contains approximately 1.2-1.5 x 10(9) cytosines, this level of 5 mdCTP incorporation corresponds to substitution of up to 16.6% of total cytosines by 5-methylcytosine, or about 100-150 new methylated cytosines per average gene.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:49:54 GMT 2025
by
admin
on
Mon Mar 31 22:49:54 GMT 2025
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| Record UNII |
B200GV71QM
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| Record Status |
Validated (UNII)
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| Record Version |
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