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M4254

Sigma-Aldrich

5-Methylcytidine

≥99%

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About This Item

Empirical Formula (Hill Notation):
C10H15N3O5
CAS Number:
2140-61-6
Molecular Weight:
257.24
EC Number:
218-390-8
MDL number:
MFCD00006548
UNSPSC Code:
41106305
PubChem Substance ID:
24896915
NACRES:
NA.51

Assay

≥99%

form

powder

mp

212-215 °C (dec.) (lit.)

solubility

water: 25 mg/mL, clear, colorless

SMILES string

CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N

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

InChI key

ZAYHVCMSTBRABG-JXOAFFINSA-N

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General description

5-Methylcytidine is a component of RNA in Escherichia coli. It is present in the RNA of plant, animal and bacterial origin. It is one of the C derivative present in transfer RNA (tRNA).

Application

5-Methylcytidine has been used as a standard for deriving the calibration curve in reversed phase high performance liquid chromatography (RP-HPLC).
5-Methylcytidine is used in studies of DNA methylation processes (epigenetics).

Biochem/physiol Actions

5-Methylcytidine is an alkylated pyrimidine plays an important role enhancing the stacking in A- and B- helices of nucleic acid, results in increase of the melting temperature and improves thermal stability leading to structural stabilization.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marija Kojic et al.
Nature communications, 9(1), 3195-3195 (2018-08-12)
Cerebellar ataxias are severe neurodegenerative disorders with an early onset and progressive and inexorable course of the disease. Here, we report a single point mutation in the gene encoding Elongator complex subunit 6 causing Purkinje neuron degeneration and an ataxia-like
Michael C Breadmore et al.
Electrophoresis, 25(10-11), 1615-1622 (2004-06-10)
The electrophoretic separation of ribavirin and 5-methylcytidine (internal standard) by capillary electrophoresis was examined. Separation was achieved using reverse polarity in a 100 mM borate electrolyte, pH 9.1, with 5 mM spermine added to reduce the electroosmotic flow. Sample preparation
K Itoh et al.
Clinica chimica acta; international journal of clinical chemistry, 234(1-2), 37-45 (1995-01-31)
A monoclonal antibody against 5-methylcytidine was prepared and characterized. This antibody, termed AMC, was reactive with compounds that had 5-methylcytosine structure (i.e. 5-methyl-2'-deoxycytidine, 5-methylcytidine and 5-methylcytosine). AMC had the highest reactivity to 5-methyl-2'-deoxycytidine among reactive compounds and had no or
Maria Beatrice Bitonti et al.
Journal of experimental botany, 53(371), 1047-1054 (2002-04-25)
Chromatin organization, nuclear DNA methylation and endogenous zeatin localization were investigated in shoot apical meristems (SAM) during juvenile and adult phases of peach (Prunus persica (L.) Batsch). The aim was to examine the extent to which these parameters could discriminate
The Primary Structure of Transfer RNA, 252-252 (2012)
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