The oxidation of 8-oxo-7,8-dihydroguanine by iodine

Katsuhito Kino; Masayuki Morikawa; Teruhiko Kobayashi; Takanobu Kobayashi; Rie Komori; Yoshihisa Sei; Hiroshi Miyazawa

doi:10.1016/j.bmcl.2010.04.032

The oxidation of 8-oxo-7,8-dihydroguanine by iodine

Bioorg Med Chem Lett. 2010 Jun 15;20(12):3818-20. doi: 10.1016/j.bmcl.2010.04.032. Epub 2010 Apr 14.

Authors

Katsuhito Kino¹, Masayuki Morikawa, Teruhiko Kobayashi, Takanobu Kobayashi, Rie Komori, Yoshihisa Sei, Hiroshi Miyazawa

Affiliation

¹ Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, Sanuki, Kagawa, Japan. kkino@kph.bunri-u.ac.jp

PMID: 20471257
DOI: 10.1016/j.bmcl.2010.04.032

Abstract

8-Oxo-7,8-dihydroguanine was specifically oxidized by iodine with aqueous KI. Under acidic conditions, the major product was dehydro-guanidinohydantoin. Under basic conditions, two diastereoisomers of spirohydantoin were chiefly obtained. In addition, unstable diimine was detected for the first time.

MeSH terms

DNA Damage
Guanidines
Guanine / analogs & derivatives*
Guanine / analysis
Guanine / chemistry
Guanosine
Hydantoins
Iodine / chemistry*
Oxidation-Reduction
Potassium Iodide
Spiro Compounds

Substances

Guanidines
Hydantoins
Spiro Compounds
dehydroguanidinohydantoin
Guanosine
Potassium Iodide
8-hydroxyguanine
Guanine
Iodine