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852589

Sigma-Aldrich

5-(Hydroxymethyl)uracil

97%

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O3
CAS Number:
Molecular Weight:
142.11
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

powder

mp

>300 °C (lit.)

functional group

hydroxyl

SMILES string

[H]O[H].OCC1=CNC(=O)NC1=O

InChI

1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)

InChI key

JDBGXEHEIRGOBU-UHFFFAOYSA-N

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hideharu Hashimoto et al.
Nucleic acids research, 40(11), 4841-4849 (2012-03-01)
Cytosine residues in mammalian DNA occur in at least three forms, cytosine (C), 5-methylcytosine (M; 5mC) and 5-hydroxymethylcytosine (H; 5hmC). During semi-conservative DNA replication, hemi-methylated (M/C) and hemi-hydroxymethylated (H/C) CpG dinucleotides are transiently generated, where only the parental strand is
Masaki Hori et al.
Nucleic acids research, 31(4), 1191-1196 (2003-02-13)
The oxidation and deamination of 5-methylcytosine (5mC) in DNA generates a base-pair between 5-hydroxymethyluracil (5hmU) and guanine. 5hmU normally forms a base-pair with adenine. Therefore, the conversion of 5mC to 5hmU is a potential pathway for the generation of 5mC
Rafal Rozalski et al.
Free radical research, 38(11), 1201-1205 (2004-12-29)
In order to eliminate the possibility that diet may influence urinary oxidative DNA lesion levels, in our experiments we used a recently developed technique involving HPLC pre-purification followed by gas chromatography with isotope dilution mass spectrometric detection. This methodology was
Berta Mendes et al.
PloS one, 8(3), e58366-e58366 (2013-03-14)
The formation of reactive oxygen species (ROS) within cells causes damage to biomolecules, including membrane lipids, DNA, proteins and sugars. An important type of oxidative damage is DNA base hydroxylation which leads to the formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG) and 5-hydroxymethyluracil
Hideharu Hashimoto et al.
Nucleic acids research, 40(17), 8276-8284 (2012-06-29)
The mammalian DNA glycosylase--methyl-CpG binding domain protein 4 (MBD4)--is involved in active DNA demethylation via the base excision repair pathway. MBD4 contains an N-terminal MBD and a C-terminal DNA glycosylase domain. MBD4 can excise the mismatched base paired with a

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