5-Hydroxycytosine

From Wikipedia, the free encyclopedia
(Redirected from C4H5N3O2)
Jump to navigation Jump to search
5-Hydroxycytosine
File:5-hydroxycytosine.svg
Names
Preferred IUPAC name
4-Amino-5-hydroxypyrimidin-2(1H)-one
Other names
4-Amino-5-hydroxypyrimidine-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C4H5N3O2/c5-3-2(8)1-6-4(9)7-3/h1,8H,(H3,5,6,7,9) COPY
    Key: NLLCDONDZDHLCI-UHFFFAOYSA-N
  • c1c(c([nH]c(=O)n1)N)O
Properties
C4H5N3O2
Molar mass 127.103 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Hydroxycytosine is an oxidized form of cytosine that is associated with an increased frequency of C to T transition mutations, with some C to G transversions.[1] It does not distort the DNA molecule and is readily bypassed by replicative DNA polymerases.[2]

It has been shown in vitro to miscode for adenine.

5-hydroxycytosine is imperative for parallel DNA triplex formation, explaining why parallel triplexes form only at pH 6 and below.

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).