Reaction of. beta. -propiolactone with derivatives of adenine and with DNA

Journal Article · Fri Jan 01 00:00:00 EST 1982 · Carcinogenesis (N.Y.); (United States)

OSTI ID:5890849

Chen, R; Mieyal, J J; Goldthwait, D A

The reaction of deoxyadenosine with ..beta..-propiolactone produces two derivatives. One is 1-(2-carboxyethyl)-2-deoxyadenosine (CEdA). 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 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 (/sup 3/H)..beta..-propiolactone at relatively high concentrations and then acid hydrolyzed to separate 1-(2-carboxyethyl)adenine (CEA) and 7-(2-carboxyethyl)guanine (CEG), and CEA to CEG ratio of up to 0.62 was obtained. With relatively low concentrations of (/sup 3/H)..beta..-propiolactone, the yield of CEA was low with double-stranded DNA but was 5-6 fold greater with single-stranded DNA.

• Research Organization: Case Western Reserve Univ., Cleveland, OH
• DOE Contract Number: AC02-76EV02725
• OSTI ID: 5890849
• Journal Information: Carcinogenesis (N.Y.); (United States), Vol. 2:2
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
DNA
ALKYLATION
NUCLEOSIDES
EMISSION SPECTRA
INFRARED SPECTRA
ULTRAVIOLET SPECTRA
ACID HYDROLYSIS
ADENINES
FLUORESCENCE
LACTONES
NUCLEAR MAGNETIC RESONANCE
TRITIUM COMPOUNDS
AMINES
ANTIMETABOLITES
AROMATICS
AZAARENES
CHEMICAL REACTIONS
DECOMPOSITION
DRUGS
ESTERS
HETEROCYCLIC COMPOUNDS
HYDROLYSIS
LABELLED COMPOUNDS
LUMINESCENCE
LYSIS
MAGNETIC RESONANCE
NUCLEIC ACIDS
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PURINES
RESONANCE
RIBOSIDES
SOLVOLYSIS
SPECTRA
550200* - Biochemistry