Acid-mediated cleavage of oligonucleotide P3′ → N5′ phosphoramidates triggered by sequence-specific triplex formation

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 8-9, 2007, Pages 893-896

  Obika, Satoshi ^a,b   Tomizu, Masaharu ^a   Negoro, Yoshinori ^a   Osaki, Tomohisa ^a   Orita, Ayako ^a   Ueyama, Yuji ^a   Nakagawa, Osamu ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Bridged nucleic acids; DNA sensing; Homopyrimidine oligonucleotides; P N bond

Indexed keywords

5' AMINOTHYMIDINE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HYDROLYSIS; NUCLEOTIDE SEQUENCE; SYNTHESIS;

AMIDES; BASE SEQUENCE; BRIDGED COMPOUNDS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; PHOSPHORIC ACIDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 36849031219     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701505741     Document Type: Article

References (7)

1. Bannwarth, W. Solid-phase synthesis of oligodeoxynucleotides containing phosphoramidate internucleotide linkages and their specific chemical cleavage. Helv. Chim. Acta 1988, 71, 1517-1527.
2. Shchepinov, M.S.; Denissenko, M.F.; Smylie, K.J.; Wörl, R.J.; Leppin, A.L.; Cantor, C.R.; Rodi, C.P. Matrix-induced fragmentation of P3′-N5′ phosphoramidate-containing DNA: high-throughput MALDI-TOF analysis of genomic sequence polymorphisms. Nucleic Acids Res. 2001, 29, 3864-3872.
3. Wolfe, J.L.; Wang, B.H.; Kawate, T.; Stanton, V.P.; Jr. Sequence-specific dinucleotide cleavage promoted by synergistic interactions between neighboring modified nucleotides in DNA. J. Am. Chem. Soc. 2003, 125, 10500-10501.
4. Gryaznov, S.M.; Letsinger, R.L. Synthesis and properties of oligonucleotides containing aminodeoxythymidine units. Nucleic Acids Res. 1992, 20, 3403-3409.
5. Obika, S.; Nakagawa, O.;Hiroto, A.;Hari, Y.; Imanishi, T. Synthesis and properties of a novel bridged nucleic acid with a P3′ →N5′ phosphoramidate linkage, 5′-amino-2′,4′ -BNA. Chem. Commun. 2003, 2202-2203.
6. Benkovic, S.J.; Sampson, E.J. Structure - reactivity correlation for the hydrolysis of phosphoramidate monoanions. J. Am. Chem. Soc. 1971, 93, 4009-4016.
7. Synthesis of these nucleoside and oligonucleotide derivatives will be published elsewhere.