The alkylation of 2'-deoxyguanosine and of thymidine with diazoalkanes. Some observations on o-alkylation.
The reaction in ether-methanol between 2'-deoxyguanosine and diazomethane or its ethyl or n-butyl homologue gives 1-, O(6)- and 7-alkyl-2'-deoxyguanosine. N(2),O(6)-Dimethyl-2'-deoxyguanosine was also detected. The hydrolysis of the methyl and the ethyl derivatives gives the corresponding alkylguanines: the O(6)-alkyl-2'-deoxyguanosines were sequentially hydrolysed, first to 2-amino-6-alkoxypurines, subsequently to guanine. The mass spectra of O(6)-alkyl-2'-deoxyguanosines (methyl and ethyl) and of the corresponding 2-amino-6-alkoxypurines were determined. The reaction of diazomethane with thymidine afforded O(4)-methylthymidine, in addition to the previously detected 3-methylthymidine.
D000478:Alkylation; D001391:Azo Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D002854:Chromatography, Paper; D003853:Deoxyribonucleosides; D003978:Diazomethane; D006151:Guanosine; D006868:Hydrolysis; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet; D013936:Thymidine
D001391:Azo Compounds; D003853:Deoxyribonucleosides; D006151:Guanosine; D003978:Diazomethane; D013936:Thymidine