1972/02/01 by P.D. Lawley, Michael Jarman · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Physics and Astronomy · #DNA and Nucleic Acid Chemistry #Chemical Reaction Mechanisms #Origins and Evolution of Life #Guanosine #Alkylation #Chemistry #Propylene oxide #Guanine #DNA #Biochemistry #Organic chemistry #Nucleotide #Catalysis #Ethylene oxide #Gene
paper · pdf · doi:10.1042/bj1260893
openalex publication_date 1972/02/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26
1. Propylene oxide reacts with DNA in aqueous buffer solution at about neutral pH to yield two principal products, identified as 7-(2-hydroxypropyl)guanine and 3-(2-hydroxypropyl)adenine, which hydrolyse out of the alkylated DNA at neutral pH values at 37 degrees C. 2. These products were obtained in quantity by reactions between propylene oxide and guanosine or adenine respectively. 3. The reactions between propylene oxide and adenine in acetic acid were parallel to those between dimethyl sulphate and adenine in neutral aqueous solution; the alkylated positions in adenine in order of decreasing reactivity were N-3, N-1 and N-9. A method for separating these alkyladenines is described. 4. Deoxyguanylic acid sodium salt was alkylated at N-7 by propylene oxide in neutral aqueous solution. 5. The nature of the side chain in the principal alkylation products was established by mass spectrometry, and the nature of the products is consistent with their formation by the bimolecular reaction mechanism.