Abstract:
: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.
journal_name
Carcinogenesisjournal_title
Carcinogenesisauthors
Chen R,Mieyal JJ,Goldthwait DAdoi
10.1093/carcin/2.2.73subject
Has Abstractpub_date
1981-01-01 00:00:00pages
73-80issue
2eissn
0143-3334issn
1460-2180journal_volume
2pub_type
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