Synthesis and Characterization of Oligonucleotides Containing 5‘,8-Cyclopurine 2‘-Deoxyribonucleosides: (5‘R)-5‘,8-Cyclo-2‘-deoxyadenosine, (5‘S)-5‘,8-Cyclo-2‘-deoxyguanosine, and (5‘R)-5‘,8-Cyclo-2‘-deoxyguanosine
- 9 April 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in Chemical Research in Toxicology
- Vol. 12 (5) , 412-421
- https://doi.org/10.1021/tx9802668
Abstract
Radiation-induced degradation of purine and pyrimidine nucleosides gave rise to carbon-bridged cyclocompounds. Such cyclonucleosides represent a class of tandem lesions in which modification of both the base and 2-deoxyribose has occurred. A solid-phase synthetic method was designed for the incorporation of both 5‘R and 5‘S diastereoisomers of 5‘,8-cyclopurine 2‘-deoxyribonucleosides into oligodeoxynucleotides to facilitate the assessment of the biochemical and biophysical features of such lesions. We report the preparation of the phosphoramidite synthons of (5‘R)-5‘,8-cyclo-2‘-deoxyadenosine (2), (5‘S)-5‘,8-cyclo-2‘-deoxyguanosine (3), and (5‘R)-5‘,8-cyclo-2‘-deoxyguanosine (4). Fully protected compounds 10, 18, and 25 were then inserted into several oligonucleotides by automated procedures. Analysis of modified DNA oligomers 26 − 31 by electrospray mass spectrometry and enzymatic digestions with exo- and endonucleases confirmed the base compositions and the integrity of free radical-induced tandem lesions 2 − 4 that were chemically inserted.Keywords
This publication has 10 references indexed in Scilit:
- Site-Specific Introduction of (5‘S)-5‘,8-Cyclo-2‘-deoxyadenosine into OligodeoxyribonucleotidesThe Journal of Organic Chemistry, 1998
- A Novel Class of Oligonucleotide Analogues Containing 2‘-O,3‘-C-Linked [3.2.0]Bicycloarabinonucleoside Monomers: Synthesis, Thermal Affinity Studies, and Molecular ModelingJournal of the American Chemical Society, 1998
- Selective hydrolysis of damaged DNA by nuclease P1Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1997
- DNA EXCISION REPAIRAnnual Review of Biochemistry, 1996
- Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: a powerful tool for the mass and sequence analysis of natural and modified oligonucleotidesNucleic Acids Research, 1993
- Free-radical-induced formation of an 8,5′-cyclo-2′-deoxyguanosine moiety in deoxyribonucleic acidBiochemical Journal, 1986
- Partial protection of carbohydrate derivatives. part 18. simple, preparative procedure for 5'--acylribonucleosides; highly regioselective -deacylation at 2' and 3' positions of fully acylated purine and pyrimidine ribonucleoside through sodium methoxide-thf systemTetrahedron, 1985
- RADIATION CHEMISTRY OF DNA COMPONENTS. FORMATION OF THE 8,5′-CYCLO-2′,5′-DIDEOXYGUANOSINE BY GAMMA IRRADIATION OF DEAERATED AQUEOUS SOLUTIONS OF 2′-DEOXYGUANOSINE AND ITS 5′-MONOPHOSPHATE ESTERChemistry Letters, 1983
- The triisopropylsilyl group as a hydroxyl-protecting functionThe Journal of Organic Chemistry, 1980
- Cyclisation radicalaire de la desoxy-2′-adenosine en solution aqueuse, sous l'effet du rayonnement gammaTetrahedron, 1976