The reaction of guanosine and 2′-deoxyguanosine with acrolein
✍ Scribed by G. Galliani; C. Pantarotto
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 137 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The purine moiety of guanosine is known to react with epoxides and P-propiolactone at the 7-nitrogen (1, 2), with N-acetoxy-N-Z-fluorenylacetamide at the B-carbon (3); and reversibly with formaldehyde (4, 5, 6) at the amino group of the 2-position, and with 1,2-dicarbonyl
## Abstract Reaction of 2′‐deoxyguanosine with glyceraldehyde under physiological conditions leads to the formation of ammonium 2‐[9‐(2‐deoxy‐β‐D‐ribofuranosyl)‐6,9‐dihydro‐6‐oxo‐1__H__‐purin‐2‐ylamino]propionate (8). The same substance can be detected in 2′‐deoxyguanosine/glucose reaction mixtures
Glucose reacts with 2'-deoxyguanosine under physiological conditions to give the diastereomeric purine substituted trihydroxy-a-amino hexanoic acids 4 as main products. Hydrolysis of 4 leads to the guanine derivatives 6 which have been synthesized by an independent route.
Acrolein, a known mutagen, undergoes reaction in vitro under physiological conditions with both 2(')-deoxyguanosine and native DNA to give rise to exocyclic adducts of the 5,6,7,8-tetrahydropyrimido[1,2-a]purine-10(3H)-one class having an hydroxy group at either the 6 or the 8 position. Previously w