Mechanisms of formation of adducts from reactions of glycidaldehyde with 2'-deoxyguanosine and/or guanosine

…, G Kennedy, C Bleasdale, WP Watson

Index: Golding, Bernard T.; Slaich, Pritpal K.; Kennedy, Gordon; Bleasdale, Christine; Watson, William P. Chemical Research in Toxicology, 1996 , vol. 9, # 1 p. 147 - 157

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Citation Number: 49

Abstract

Convenient syntheses of rac-glycidaldehyde from rac-but-3-ene-1, 2-diol and (R)- glycidaldehyde from d-mannitol are described.(R)-Glycidaldehyde (1) reacts with guanosine in water (pH 4-11, faster reaction at higher pH) to give initially 6 (S)-hydroxy-7 (S)- (hydroxymethyl)-3-(β-d-ribofuranosyl)-5, 6, 7-trihydroimidazo [1, 2-a] purin-9 (3 H)-one (7a) and 6 (S), 7 (R)-dihydroxy-3-(β-d-ribofuranosyl)-5, 6, 7, 8-tetrahydropyrimido [1, 2-a] purin- ...

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