Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea
- 1 July 1984
- journal article
- research article
- Published by Springer Nature in Cellular and Molecular Life Sciences
- Vol. 40 (7) , 734-736
- https://doi.org/10.1007/bf01949749
Abstract
Summary The axial (ax.) and equatorial (eq.) diastereomeric forms of phosphate triesters resulting from reactions of N-ethyl, N-nitrosourea with 3 cyclic mononucleotides were analyzed by column liquid chromatography (CLC). Evidence is presented that the 2′OH group of 3′, 5′cAMP essentially contributes to the stereoselective eq. alkyl substitution, most probably by hydrogen bonding catalysis. The neighboring group direction of ethylation gives substantial support to non-random DNA alkylations by NEU.Keywords
This publication has 24 references indexed in Scilit:
- Methylation of chromosomal DNA by two alkylating agents differing in carcinogenic potentialCancer Letters, 1981
- N-acetoxy-acetylaminofluorene reacts preferentially with a control region of intracellular SV40 chromosomeNature, 1981
- Carcinogen-DNA interaction: Complexing of distamycin-A with DNA is necessary for its inhibitory effect on the N-methyl-N-nitrosourea induced methylation of DNAChemico-Biological Interactions, 1981
- The binding of benzo(a)pyrene to DNA components of differing sequence complexityInternational Journal of Cancer, 1980
- Binding of isomers of benzo[a]pyrene diol-epoxide to chromatinBiochemical and Biophysical Research Communications, 1980
- Use of anN-Alkyl-N-nitrosourea-Copper(II) Complex as Carbenium Synthon in the Synthesis of Nucleotide EstersSynthesis, 1974
- Stereochemistry of oxidation of tribalent phosphorus and configurational assignments in 2-substituted 1,3,2-dioxaphosphorinanesJournal of the American Chemical Society, 1973
- 2'-O-alkyl polynucleotides. I. Novel procedure for the synthesis of 2'-O-alkyl nucleotidesBiochemistry, 1972
- Instability of alkylated deoxyribonucleic acid in relation to the mechanism of chemical mutagenesisBiochimica et Biophysica Acta, 1961
- Voyage of the Discovery IINature, 1952