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Oxidative hydrolysis of a cyclic 1,N2-propano-2′-deoxyguanosine, an adduct of 2′-deoxyguanosine with acetaldehyde or crotonaldehyde

✍ Scribed by Magoichi Sako; Shinsuke Inagaki; Yukihiro Esaka; Yoshihiro Deyashiki

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
127 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The SO 4 --oxidation of cyclic 1,N 2 -propano-2%-deoxyguanosine, chemo-and regioselectively produced in the reaction of 2%-deoxyguanosine with excessive acetaldehyde or crotonaldehyde, resulted in the smooth formation of (4-hydroxy-5hydroxymethyltetrahydrofuran-2-ylimino)-(4-hydroxy-6-methyltetrahydropyrimidin-2-ylideneamino)acetic acid, 3-(4-hydroxy-5hydroxymethyltetrahydrofuran-2-yl)-6-methyl-3H-1,3,4,5,8a-pentaazacyclopenta[b]naphthalen-9-one, and 2%-deoxyguanosine even under neutral conditions. The formation of the guanine-ring opened product during the reaction is very interesting and appears to closely relate to the mechanisms for the point-mutations of DNA by these mutagenic and carcinogenic aldehydes.

📜 SIMILAR VOLUMES

Smooth and selective formation of the cy
Smooth and selective formation of the cyclic 1,N2-propano adducts in the reactions of guanine nucleosides and nucleotides with acetaldehyde
✍ Magoichi Sako; Isamu Yaekura; Yoshihiro Deyashiki 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 71 KB

The treatment of guanine nucleosides and nucleotides with excess acetaldehyde in pH 8.0 phosphate buffer containing a basic amino acid such as arginine and lysine resulted in the smooth and selective formation of the corresponding cyclic 1,N 2 -propano adducts even under mild conditions.