A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF DIOXOLANE NUCLEOSIDE ANALOGS
Tekijät: EFIMTSEVA EV, MIKHAILOV SN, MESHKOV SV, LONNBERG H
Kustantaja: MUNKSGAARD INT PUBL LTD
Julkaisuvuosi: 1992
Lehti:: Acta Chemica Scandinavica
Tietokannassa oleva lehden nimi: ACTA CHEMICA SCANDINAVICA
Lehden akronyymi: ACTA CHEM SCAND
Vuosikerta: 46
Numero: 11
Aloitussivu: 1122
Lopetussivu: 1126
Sivujen määrä: 5
ISSN: 0904-213X
DOI: https://doi.org/10.3891/acta.chem.scand.46-1122
Tiivistelmä
Four novel nucleoside analogues, viz. the cis and trans isomers of 4-hydroxymethyl-2(uracil-1-ylmethyl)-1,3-dioxolane and 2-(adenin-9-ylmethyl)-4-hydroxymethyl-1,3-dioxolane, have been prepared. Alkylation of the sodium salts of uracil and adenine with 4-benzoyloxymethyl-2-bromomethyl-1,3-dioxolane, separation of the resulting cis and trans isomers by adsorption and reversed-phase chromatography, and deprotection with methanolic ammonia yielded the desired analogues of 2',3'-dideoxyribo-nucleosides. The structures of the products were verified by NMR spectroscopy, and the kinetics of their acid-catalyzed hydrolysis were studied.
Four novel nucleoside analogues, viz. the cis and trans isomers of 4-hydroxymethyl-2(uracil-1-ylmethyl)-1,3-dioxolane and 2-(adenin-9-ylmethyl)-4-hydroxymethyl-1,3-dioxolane, have been prepared. Alkylation of the sodium salts of uracil and adenine with 4-benzoyloxymethyl-2-bromomethyl-1,3-dioxolane, separation of the resulting cis and trans isomers by adsorption and reversed-phase chromatography, and deprotection with methanolic ammonia yielded the desired analogues of 2',3'-dideoxyribo-nucleosides. The structures of the products were verified by NMR spectroscopy, and the kinetics of their acid-catalyzed hydrolysis were studied.
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