2476-56-4Relevant academic research and scientific papers
Photochemical generation of oligodeoxynucleotide containing a C4′-oxidized abasie site and its efficient amine modification: Dependence on structure and microenvironment
Usui, Kazuteru,Aso, Mariko,Fukuda, Mitsuhiro,Suemune, Hiroshi
, p. 241 - 248 (2008/09/19)
(Chemical Equation Presented) 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.
SOLID PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING 3'-THIOTHYMIDINE
Cosstick, Richard,Vyle, Joseph S.
, p. 4693 - 4696 (2007/10/02)
A 5'-O-monomethoxytritylthymidine-3'-S-thiophosphoramidite (3) has been used to prepare oligodeoxynucleotides containing 3'-thiothymidine on a solid phase support.The intermediate thiophosphites are most efficiently oxidised using tetrabutylammonium periodate.
Nucleotides. Part XXVII. BisPhosphorochloridate, a New Versatile Phosphorilating Agent in Nucleotide Chemistry
Himmelsbach, Frank,Charubala, Ramamurthy,Pfleiderer, Wolfgang
, p. 1286 - 1295 (2007/10/02)
A new, versatile phosphorilating agent, bis phosphorochloridate (3), has been prepared and is used for 3'- and/or 5'-phosphorylations of nucleotides.The resulting bis phosphotriesters are versatile synthons
4,4',4''-Tris(levulinoyloxy)trityl as a New Type of Primary Hydroxyl Protecting Group
Sekine, Mitsuo,Hata, Tsujiaki
, p. 336 - 339 (2007/10/02)
The 4,4',4''-tris(levulinoxy)trityl (TLTr) group was introduced selectively on the 5'-oxygen of thymidine by use of in situ generated 4,4',4''-tris(levulinoyloxy)trityl bromide.The TLTr group was found to be sufficiently stable to acids and readily removed by hydrazinolysis followed by warming to 50 deg C in pyridine-acetic acid without damage of other protecting groups such as the O-acetyl and 4,4'-dimethoxytrityl groups.The utility of this new protecting group was demonstrated by the successful synthesis of thymidylyl(3'-5')thymidine where the TLTr group was employed as 5'-hydroxyl-protecting group.
AN INVESTIGATION OF SEVERAL DEOXYNUCLEOSIDE PHOSPHORAMIDITES USEFUL FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES
McBride, L. J.,Caruthers, M. H.
, p. 245 - 248 (2007/10/02)
Various deoxynucleoside N,N-dialkylaminomethoxyphosphines were examined for stability and reactivity in deoxyoligonucleotide synthesis.Of those examined, the N-morpholino and N,N-diisopropylamino derivatives most completely satisfied all criteria.
