5-Methyl-2'-deoxycytidine

5-Methyl-2'-deoxycytidine (5mdC) is an endogenous substrate of DNA methyltransferases (such as mammalian 5-C-MTase) and binds to DNA dependent on the formation of DNA stem-loop structures. 5-Methyl-2'-deoxycytidine guides de novo DNA methylation by acting as a methylation mark and activates the methylation of adjacent CpG sites in single-stranded DNA through cis action. 5-Methyl-2'-deoxycytidine regulates DNA methylation patterns by recruiting methyltransferases to specific chromatin regions, affecting chromatin condensation and gene expression. Its distribution in plant cells is related to cell proliferation and differentiation stages. The methylation level of 5-Methyl-2'-deoxycytidine is low in proliferating cells and high in differentiated cells[1][2][3].

Product Specifications

CAS Number

[838-07-3]

Product Name Alternative

5-Methyldeoxycytidine

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

DNA Methyltransferase; Endogenous Metabolite

Type

Natural Products

Related Pathways

Epigenetics; Metabolic Enzyme/Protease

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Others

Assay Protocol

https://www.medchemexpress.com/5-methyl-2-deoxycytidine.html

Purity

99.87

Solubility

DMSO : ≥ 100 mg/mL|H2O : 100 mg/mL (ultrasonic)

Smiles

OC[C@@H]1[C@@H](O)C[C@H](N2C(N=C(N)C(C)=C2)=O)O1

Molecular Formula

C10H15N3O4

Molecular Weight

241.25

Precautions

H302, H315, H319, H335

References & Citations

[1]Christman JK, et al. 5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation. Proc Natl Acad Sci U S A. 1995 Aug 1;92 (16) :7347-51.|[2]Testillano PS, et al. The 5-methyl-deoxy-cytidine (5mdC) localization to reveal in situ the dynamics of DNA methylation chromatin pattern in a variety of plant organ and tissue cells during development. Physiol Plant. 2013 Sep;149 (1) :104-13.|[3]Magaña AA, et al. High-performance liquid chromatography determination of 5-methyl-2'-deoxycytidine, 2'-deoxycytidine, and other deoxynucleosides and nucleosides in DNA digests. Anal Biochem. 2008 Mar 15;374 (2) :378-85.