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5-Methyl-2'-deoxycytidine

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Products Intro: Product Name:5-Methyl-2'-deoxycytidine
CAS:838-07-3
Purity:98% Package:10g;100g;500g;1kg;5kg;10kg,100kg,1ton Remarks:Nucleosides
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CAS:838-07-3
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CAS:838-07-3
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CAS:838-07-3
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5-Methyl-2'-deoxycytidine manufacturers

  • 5-Methyl-2"-deoxycytidine
  • 5-Methyl-2
  • $15.00 / 1KG
  • 2021-08-12
  • CAS:838-07-3
  • Min. Order: 1KG
  • Purity: 99%+ HPLC
  • Supply Ability: Monthly supply of 1 ton
5-Methyl-2'-deoxycytidine Basic information
Product Name:5-Methyl-2'-deoxycytidine
Synonyms:5-METHYL-DC;5-METHYL-2'-DEXOYCYTIDINE;4-AMINO-1-[(2R,4S,5R)-4-HYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5-METHYL-PYRIMIDIN-2-ONE;2’-deoxy-5-methyl-cytidin;5-Me-2'-deoxycytidine;2'-Deoxy-5-methylcytidine, ≥99%(HPLC);2'-Deoxy-5-Me-Cytidine;5-methyldeoxycytidine
CAS:838-07-3
MF:C10H15N3O4
MW:241.24
EINECS:212-655-1
Product Categories:Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
Mol File:838-07-3.mol
5-Methyl-2'-deoxycytidine Structure
5-Methyl-2'-deoxycytidine Chemical Properties
Melting point 217-219 °C(lit.)
Boiling point 492.8±55.0 °C(Predicted)
density 1?+-.0.1 g/cm3(Predicted)
refractive index 44 ° (C=1.4, H2O)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly)
form Powder
pkapK1:4.33 (25°C)
color White to Off-white
Optical Rotation41.1°(C=0.009986 g/ml H2O)
Water Solubility Soluble in water.
Stability:Hygroscopic
InChIInChI=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
InChIKeyLUCHPKXVUGJYGU-XLPZGREQSA-N
SMILESOC[C@H]1O[C@@H](N2C=C(C)C(N)=NC2=O)C[C@@H]1O
CAS DataBase Reference838-07-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-24/25
WGK Germany 3
RTECS HA3860000
HS Code 29389090
MSDS Information
ProviderLanguage
SigmaAldrich English
5-Methyl-2'-deoxycytidine Usage And Synthesis
Description5-Methyl-2'-deoxycytidine is a nucleoside analogue that inhibits the synthesis of DNA. 5-Methyl-2'-deoxycytidine prevents methylation of guanine, which disrupts the binding of guanine nucleotide-binding proteins to the dna template and prevents polymerase chain reactions. 2'-Deoxy-5-methylcytidine is also a methyltransferase inhibitor, which means it blocks the enzyme responsible for adding methyl groups to cytosine molecules.
Chemical PropertiesWhite Solid
Uses5-Methyl-2'-deoxycytidine is a pyrimidine nucleoside that when incorporated into single-stranded DNA can act in cis to signal de novo DNA methylation. It has been used in epigenetics research to investigate the dynamics of DNA methylation pattern in the control of gene expression.
Uses5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation.
UsesA Cytidine (C998300) analog and also an isostere of Thymidine (T412000).
DefinitionChEBI: 5-methyl-2'-deoxycytidine is a 2'-deoxycytidine.
General DescriptionGiel-Pietraszuk et al. developed a new method for quantification of 5-methyl-2'-deoxycytidine (m5C) in the DNA. The technique is based on the conversion of m5C into fluorescent 3, N4-etheno-5-methyl-2'-deoxycytidine (εm5C) and its identification by reversed-phase high-performance liquid chromatography (RP-HPLC)[1].The measurement of 5-meC and 5-medC in urine may help assess changes in DNA methylation status in the whole body and investigate the DNA demethylation mechanism in vivo. 5-MedC was first detected in urine using an inhibition ELISA method;12 however, because ELISA may suffer from poor selectivity and sensitivity, later urinary measurements of 5-medC were developed mainly based on the chromatographic techniques[2].
Synthesis
Thymidine

50-89-5

5-Methyl-2'-deoxycytidine

838-07-3

The general procedure for the synthesis of 4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2,4(1H,3H)-diones, using 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1H)-one as a starting material was carried out as follows. DMF a nucleoside solution was prepared (substrate concentration of 0.3 M, except for compounds 3 and 4, which was 0.05 M) to which PyAOP (1.6 eq.) and DBU (1.6 eq.) were added. The reaction mixture was stirred at 20 °C for 1 min. Subsequently, N-nucleophilic reagent (4 eq. dissolved in THF if 1a was used, or concentrated NH4OH, 10 eq.) was added to the reaction system. The reaction continued to be stirred at 20 °C for 5 min to 4 h and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the solution was concentrated under vacuum. Separation by fast column chromatography on silica gel afforded purified forms of the target product 5MedC and its oxidized derivatives 1'-20'.

References[1] Ma?gorzata Giel-Pietraszuk. “Quantification of 5-methyl-2’-deoxycytidine in the DNA.” Acta biochimica Polonica 62 2 (2015): 281–6.
[2] Chiung-Wen Hu. “Direct Analysis of 5-Methylcytosine and 5-Methyl-2′-deoxycytidine in Human Urine by Isotope Dilution LC-MS/MS: Correlations with N-Methylated Purines and Oxidized DNA Lesions.” Chemical Research in Toxicology 25 2 (2012): 462–470.
5-Methyl-2'-deoxycytidine Preparation Products And Raw materials
Raw materialsThymidine-->N,N-Dimethylformamide-->Ammonium hydroxide-->DBU
Preparation Products5-METHYLCYTOSINE-->5'-O-(4,4'-DIMETHOXYTRITYL)-N4-BENZOYL-5-METHYL-2'-DEOXYCYTIDINE
Tag:5-Methyl-2'-deoxycytidine(838-07-3) Related Product Information
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