Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N
InChI
InChIKey=ZAYHVCMSTBRABG-JXOAFFINSA-N
InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
5-methyl cytidine has been indicated in the controlling mechanism for the genetic change, which leads to cancer. Human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD) with specificity for single stranded DNA, can extensively deaminate human nuclear DNA. It was discovered that A3A among all human PCDs can deaminate 5-methylcytidine in a variety of single stranded DNA substrates both in vitro and in transfected cells almost as efficiently as cytidine itself. As 5MeCpG deamination hotspots characterize many genes associated with cancer it was made suggestion that A3A is a major player in the onset of cancer.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of urethan induced lung tumour growth in strain A mice by 5-methyl cytidine. | 1980 |
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| The nature of cancer and the mechanisms of its control: a review. | 1980 |
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| Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. | 1995 Jan 31 |
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| Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides. | 2001 Apr 20 |
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| Measurement of genome wide DNA methylation by reversed-phase high-performance liquid chromatography. | 2002 Jun |
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| Distinct nuclear organization, DNA methylation pattern and cytokinin distribution mark juvenile, juvenile-like and adult vegetative apical meristems in peach (Prunus persica (L.) Batsch). | 2002 May |
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| The binding sites for the chromatin insulator protein CTCF map to DNA methylation-free domains genome-wide. | 2004 Aug |
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| Kilo-scale synthesis process for 2'-O-(2-methoxyethyl)-pyrimidine derivatives. | 2005 |
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| Modifications in small interfering RNA that separate immunostimulation from RNA interference. | 2008 Mar 1 |
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| Effective, homogeneous and transient interference with cytosine methylation in plant genomic DNA by zebularine. | 2009 Feb |
|
| Specific loss of histone H3 lysine 9 trimethylation and HP1gamma/cohesin binding at D4Z4 repeats is associated with facioscapulohumeral dystrophy (FSHD). | 2009 Jul |
|
| DNA methyltransferase-mediated transcriptional silencing in malignant glioma: a combined whole-genome microarray and promoter array analysis. | 2009 Jul 23 |
|
| Effect of IVF and laser zona dissection on DNA methylation pattern of mouse zygotes. | 2009 Sep-Oct |
|
| Multi-site-specific 16S rRNA methyltransferase RsmF from Thermus thermophilus. | 2010 Aug |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: As several TP53 CpG methylation sites are mutational hotspots in cancer, an oligodeoxynucleotide corresponding to part of exon 8 was synthesized with 5-methylcytidine (5MeC) incorporated at two known sites of methylation in codons 273 and 282. Following incubation with purified myc-His6-tagged A3A (human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD)) and recovery of products by standard PCR, both 5MeC and C were readily deaminated in a comparable manner. Given that 5MeC is deaminated by A3A the singularity of 5MeCpG mutation hotspots in cancer probably has more to do with the relative efficiency of T:G mismatch repair compared to highly efficient U:G repair initiated by UNG.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:45:07 GMT 2023
by
admin
on
Sat Dec 16 09:45:07 GMT 2023
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| Record UNII |
TL9PB228DC
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| Record Status |
Validated (UNII)
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| Record Version |
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363933
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92918
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2140-61-6
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DTXSID401016977
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5-Methylcytidine
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TL9PB228DC
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218-390-8
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