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414174

Sigma-Aldrich

5-Formyluracil

98%

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Empirical Formula (Hill Notation):
C5H4N2O3
CAS Number:
Molecular Weight:
140.10
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

powder

mp

>300 °C (dec.) (lit.)

SMILES string

O=CC1=CNC(=O)NC1=O

InChI

1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10)

InChI key

OHAMXGZMZZWRCA-UHFFFAOYSA-N

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5-Formyluracil 98%

414174

5-Formyluracil

5-Methylquinoxaline 98%

272310

5-Methylquinoxaline

5-Chlorosalicylaldehyde 98%

447706

5-Chlorosalicylaldehyde

5-Bromovaleronitrile 98%

B83207

5-Bromovaleronitrile

form

powder

form

-

form

solid

form

liquid

mp

>300 °C (dec.) (lit.)

mp

20-21 °C (lit.)

mp

100-102 °C (lit.)

mp

-

Application

5-Formyluracil may be used for the preparation of covalently linked base with 5-aminocytosine pair via Schiff base formation.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Katsuhito Kino et al.
Biochemistry, 43(10), 2682-2687 (2004-03-10)
5-Formyluracil (fU) is a major thymine lesion produced by reactive oxygen radicals and photosensitized oxidation. Although this residue is a potentially mutagenic lesion and is removed by several base excision repair enzymes, it is unknown whether fU is the substrate
Pingfang Liu et al.
DNA repair, 2(2), 199-210 (2003-01-18)
The oxidation of the thymine methyl group can generate 5-formyluracil (FoU). Template FoU residues are known to miscode, generating base substitution mutations. The repair of the FoU lesion is therefore important in minimizing mutations induced by DNA oxidation. We have
Yinsheng Wang et al.
Journal of the American Society for Mass Spectrometry, 13(10), 1190-1194 (2002-10-22)
2-Aminoimidazolone and 5-formyluracil are major one-electron photooxidation products of guanine and thymine in oligodeoxynucleotides (ODNs). Herein we report the HPLC isolation and tandem mass spectrometric characterization of ODNs carrying those types of base modifications. Collision-activated dissociation (CAD) of the deprotonated
Q M Zhang
Journal of radiation research, 42(1), 11-19 (2001-06-08)
Ionizing radiation induces a wide variety of modifications to purine and pyrimidine residues. The exocyclic methyl group of thymine does not escape oxidative damage. Any 5-hydroperoxymethyluracil produced is spontaneously decomposed to form 5-formyluracil (5-foU) and 5-hydroxymethyluracil. The yield of 5-foU
Hiroyuki Kamiya et al.
Mutation research, 513(1-2), 213-222 (2001-11-24)
Oxidatively damaged thymine, 5-formyluracil (5-fU), was incorporated into a predetermined site of double-stranded shuttle vectors. The nucleotide sequences in which the modified base was incorporated were 5'-CFTAAG-3' and 5'-CTFAAG-3' (F represents 5-fU), the recognition site for the restriction enzyme AflII

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