Document Detail

Photochemical generation of oligodeoxynucleotide containing a C4'-oxidized abasic site and its efficient amine modification: dependence on structure and microenvironment.
MedLine Citation:
PMID:  18062702     Owner:  NLM     Status:  MEDLINE    
Bleomycin-induced oxidative DNA damage under limited oxygen conditions results in the formation of the C4'-oxidized abasic site (1). We synthesized the oligodeoxynucleotides (ODN) 5, which contains 4'-o-nitrobenzyloxythymidine (3), and 6, which contains 2-nitrobenzyloxy-4'-methoxy-2'-deoxy-d-ribofuranoside (4), as the caged precursors of 7, an ODN containing 1, to study its reactivity with amines. Photoirradiation of the single- and double-stranded 5 led to the formation of 7. Uncaging of the duplex was faster and the yield of 7 was higher with the double-stranded than with the single-stranded ODN. It was suggested that a low dielectric environment of the o-nitrobenzyloxy group in the minor groove of the duplex might accelerate the uncaging rate. Similarly, 6 and its duplex yielded 7 by photoirradiation. However, the yields of 7 were lower than those of 5, and duplex formation slowed the uncaging rate. Reaction of the obtained 7 with an amine resulted in the formation of the lactam 2b in good yield in both single- and double-stranded forms, showing that amine modification of biomolecules by an ODN containing 1 is possible under physiologic conditions.
Kazuteru Usui; Mariko Aso; Mitsuhiro Fukuda; Hiroshi Suemune
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-12-07
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Jan 
Date Detail:
Created Date:  2007-12-28     Completed Date:  2008-03-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  241-8     Citation Subset:  IM    
Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
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MeSH Terms
Amines / chemistry*,  radiation effects*
Binding Sites
Molecular Structure
Nucleic Acid Conformation
Oligodeoxyribonucleotides / chemical synthesis*,  chemistry,  radiation effects*
Time Factors
Ultraviolet Rays*
Reg. No./Substance:
0/Amines; 0/Oligodeoxyribonucleotides

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