Reaction of arene oxides with nucleosides.
Inosine was reacted with phenanthrene-9,10-oxide and 7,12-dimethylbenz(a)anthracene-5,6-oxide (DMBA-5,6-oxide) to yield the corresponding N-1-alkylinosines. They were shown to undergo hydrolysis to 5-amino-4-imidazole-N-alkylcarboxamide ribosides when heated in the presence of sodium carbonate. Guanosine was reacted with DMBA-5,6-oxide to yield a mixture of N-7-alkylguanines along with a smaller amount of an orcine positive product exhibiting an ultraviolet spectrum resembling that of DMBA-5,6-dihydrodiol.
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000031:analogs & derivatives / Q000378:metabolism; D000478:Alkylation; D001551:Benz(a)Anthracenes / Q000031:analogs & derivatives; D055598:Chemical Phenomena; D002621:Chemistry; D006151:Guanosine / Q000031:analogs & derivatives / Q000378:metabolism*; D066298:In Vitro Techniques; D007288:Inosine / Q000031:analogs & derivatives / Q000378:metabolism*; D010616:Phenanthrenes / Q000378:metabolism*
D001551:Benz(a)Anthracenes; D010616:Phenanthrenes; D006151:Guanosine; D015127:9,10-Dimethyl-1,2-benzanthracene; D007288:Inosine