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MilliporeSigma

M6751

5-Methylcytosine hydrochloride

≥99%, synthetic (organic), crystalline powder

Sinónimos:

4-Amino-2-hydroxy-5-methylpyrimidine

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250 MG

$169.00

1 G

$508.00

$169.00


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Fórmula empírica (notación de Hill):
C5H7N3O · HCl
Número CAS:
Peso molecular:
161.59
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
261-223-9
MDL number:

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Nombre del producto

5-Methylcytosine hydrochloride, ≥99%

InChI key

ANWMULVRPAUPJT-UHFFFAOYSA-N

InChI

1S/C5H7N3O.ClH/c1-3-2-7-5(9)8-4(3)6;/h2H,1H3,(H3,6,7,8,9);1H

SMILES string

O=C1NC(N)=C(C)C=N1.[H]Cl

biological source

synthetic (organic)

assay

≥99%

form

crystalline powder

solubility

water: 50 mg/mL, clear to slightly hazy, colorless

Quality Level

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1 of 4

Este artículo
C3506I6875284769
biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

Quality Level

200, 300

Quality Level

200

Quality Level

200

Quality Level

100

assay

≥99%

assay

≥99%

assay

≥99% (TLC)

assay

98%

form

crystalline powder

form

powder

form

powder

form

-

solubility

water: 50 mg/mL, clear to slightly hazy, colorless

solubility

0.5 M HCl: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

solubility

formic acid: 50 mg/mL

solubility

water: soluble 50 mg/mL, clear to slightly hazy, colorless to light yellow

Application

5-Methylcytosine hydrochloride has been used as standard in high performance liquid chromatography (HPLC) for the estimation of global methylation rates.[1] It has also been used in high-resolution mass spectroscopic analysis.[2]
5-Methylcytosine is used in studies of DNA methylation processes (epigenetics).

Biochem/physiol Actions

5-Methylcytosine mediates gene expression, genomic imprinting and inhibition of transposable elements.[3] It is closely associated with translational fidelity and tRNA recognition.[4]

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Daniel Renciuk et al.
Nucleic acids research, 41(21), 9891-9900 (2013-08-22)
5-Hydroxymethylcytosine (5-hmC) was recently identified as a relatively frequent base in eukaryotic genomes. Its physiological function is still unclear, but it is supposed to serve as an intermediate in DNA de novo demethylation. Using X-ray diffraction, we solved five structures
Absolute quantification of RNA or DNA using acid hydrolysis and mass spectrometry
Lowenthal MS, et al.
Analytical Chemistry, 6, 824-824 (2019)
Widespread occurrence of 5-methylcytosine in human coding and non-coding RNA
Squires JE, et al.
Nucleic Acids Research, 40(11), 5023-5033 (2012)
Rachel Deplus et al.
The EMBO journal, 32(5), 645-655 (2013-01-29)
TET proteins convert 5-methylcytosine to 5-hydroxymethylcytosine, an emerging dynamic epigenetic state of DNA that can influence transcription. Evidence has linked TET1 function to epigenetic repression complexes, yet mechanistic information, especially for the TET2 and TET3 proteins, remains limited. Here, we
Myunggon Ko et al.
Nature, 497(7447), 122-126 (2013-04-09)
TET (ten-eleven-translocation) proteins are Fe(ii)- and α-ketoglutarate-dependent dioxygenases that modify the methylation status of DNA by successively oxidizing 5-methylcytosine to 5-hydroxymethylcytosine, 5-formylcytosine and 5-carboxycytosine, potential intermediates in the active erasure of DNA-methylation marks. Here we show that IDAX (also known

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