The reaction of beta-propiolactone with derivatives of adenine and with DNA.
The reaction of deoxyadenosine with beta-propiolactone produces two derivatives. One is 1-(2-carboxyethyl)-2'-deoxyadenosine (CEdA) first described by Maté, et al. The proposed structure for the other is 3-(beta-D-2-deoxyribosyl)-7,8-dihydropyrimido-[2,l-i]purine-9-one (dDPP). Spectral characteristics of both compounds are presented. These include u.v. spectra of each in acidic, neutral and alkaline solutions, i.r. spectra, fluorescence spectra, and n.m.r. spectra. The extinction coefficient for CEdA is 12,900 M--1cm--1 at 258 nm and that for dDPP is 12,400 M--1cm--1 at 305 nm. The dDPP can be converted to CEdA by mild acid hydrolysis, and the CEdA can be converted to dDPP by reaction with a carbodiimide derivative. When poly A was reacted with beta-propiolactone, the yield of dDPP in the polymer was 7-9%. When double-stranded DNA was alkylated by [3H]beta-propiolactone at relatively high concentrations and then acid hydrolyzed to separate 1-(2-carboxyethyl)adenine (CEA) and 7-(2-carboxyethyl)guanine (CEG), a CEA to CEG ratio of up to 0.62 was obtained. With relatively low concentrations of [3H]beta-propiolactone, the yield of CEA was low with double-stranded DNA but was 5--6 fold greater with single-stranded DNA.
D000225:Adenine / Q000031:analogs & derivatives*; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D011420:Propiolactone; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D007783:Lactones; D011420:Propiolactone; D004247:DNA; D000225:Adenine