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The reaction of guanosine and deoxyguanosine with glycidaldehyde

✍ Scribed by B.M. Goldschmidt; T.P. Blazej; B.L. Van Duuren

Publisher
Elsevier Science
Year
1968
Tongue
French
Weight
201 KB
Volume
9
Category
Article
ISSN
0040-4039

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✦ Synopsis

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

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## 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

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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.