5-formyl dU (5-foU)

FULL NAME: 5-formyl-2'-deoxyuridine


DESCRIPTION:
5-Formyluracil (fU) is a major thymine lesion produced by reactive oxygen radicals and photosensitized oxidation. Oxidation of the methyl group of thymine yields and 5-formyluracil (5-foU) as major product. Mutations induced by 5-formyl-2'-deoxyuridine in Escherichia coli include base substitutions that can arise from mispairs of 5-formyluracil with guanine, cytosine and thymine. 5-formyl-2'-deoxyuridine (5-fodUrd) supplied to the growth medium of Escherichia coli induces several base substitutions at different frequencies at position 461 in the lacZ gene in the following order: A:T-->G:C > G:C-->A:T > G:C-->T:A >> A:T-->T:A > A:T-->C:G. No induction of G:C-->C:G transversions was observed. Single-stranded oligonucleotides containing 5-formyl-2'-deoxyuridine (fdU) can crosslink the peptides derived from the DNA binding site of RecA protein through a Schiff base formation. The nucleoside 5-formyl-2'-deoxyuridine has been used as a starting point for the generation of novel 5-substituted pyrimidine nucleosides that are shown to possess significant antiviral activity against two representative orthopoxviruses, namely vaccinia virus and cowpox virus.

DAMAGE TYPE: oxidative damage


DNA DAMAGE SOURCE(S) (MAIN):
reactive oxygen species (ROS)


DNA DAMAGE EFFECT(S) (MAIN):
A→G transition
G→A transition
mutagenesis
point mutation
substitution
transition


DNA DAMAGE EFFECT(S) (MINOR):
A→C transversion
A→T transversion
G→T transversion
mutagenesis
point mutation
substitution
transversion


PATHWAYS:
base excision repair (BER)
heterochromatin formation


DNA repair protein(s) related to damage:
Fpg (MutM)
Mug
SMUG1
AlkA
Nth (endo III)
MBD4 (MED1)
NTHL1
Nei (endo VIII)
NTHL1


Last modification date: Oct. 17, 2011