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The reaction of propane sultone with cuanosine, adenosine, and related compounds
Author(s) -
Goldschmidt B. M.,
Frenkel K.,
Van Duuren B. L.
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110510
Subject(s) - chemistry , guanosine , deoxyguanosine , nucleoside , yield (engineering) , alkyl , propane , purine , adenosine , organic chemistry , nucleic acid , medicinal chemistry , stereochemistry , adduct , biochemistry , materials science , metallurgy , enzyme
Abstract Propane sultone (3‐hydroxypropanesulfonic acid‐γ‐lactone) which is a monofunctional directacting alkylating carcinogen, has been shown to react irreversibly with DNA from various sources in vitro. It reacts with guanosine in DMSO to yield the N‐7 alkyl nucleoside, while reaction with 2′‐deoxyguanosine yields the corresponding N‐7 alkyl purine. Evidence for the structure of these products and of one formed when adenosine and propane sultone react is presented.