6-(Levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl and 2-(Levulinyloxymethyl)-5-methoxy-4-nitrobenzoyl Groups as Novel Base-Labile Groups for 5′-Hydroxy Protection in Solid-Phase Oligonucleotide Synthesis

Author:

Kamaike Kazuo12,Namiki Takashi1,Kawashima Etsuko1

Affiliation:

1. a School of Pharmacy , Tokyo University of Pharmacy and Life Science , Tokyo, Japan

2. b School of Pharmacy , Tokyo University of Pharmacy and Life Science , 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan

Publisher

Informa UK Limited

Subject

Genetics,Molecular Medicine,Biochemistry,General Medicine

Reference12 articles.

1. a) Matteucci, M.D.; Caruthers, M.H. Synthesis of deoxyoligonucleotides on a polymer support. J. Am. Chem. Soc.1981,103, 3185–3191; b) Tanaka, T.; Letsinger, R.L. Syringe method for stepwise chemical synthesis of oligonucleotides. Nucleic Acids Res.1982,10, 3249–3260

2. a) Reese, C.B.; Skone, P.A. Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions. Nucleic Acids Res.1985,13, 5215–5231; b) Hirao, I.; Ishikawa, M.; Miura, K. Solid-phase synthesis of oligoribonucleotides. Nucleic Acids Res. Symp. Ser.1985,16, 173–176; c) Christodoulou, C.; Agrawal, S.; Gait, M.J. Incompatibility of acid-labile 2′ and 5′ protecting groups for solid-phase synthesis of oligoribonucleotides. Tetrahedron Lett.1986,27, 1521–1522

3. a) Beaucage, S.L.; Iyer, R.P. Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron1992,48, 2223–2311; b) Bergmann, F.; Pfleiderer, W. Nucleotides. Part XLI. (=2−{5-(Dimethylamino)naphthalen-l-yl]sulfonyl}ethoxycarbonyl; Dnseoc) group for protection of the 5′-Hydroxy function of oligoribonucleotide synthesis. Helv. Chim. Acta1994,77, 203–215; c) idem., Nucleotides. Part XLII. The 2-dansylethoxycarbonyl (=2−{[5−(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxycarbonyl; Dnseoc) group for protection of the 5′-Hydroxy function of oligoribonucleotide synthesis, ibid.1994,77, 481–501; d) Bergmann, F.; Pfleiderer, W. Nucleotides. Part XLIII. Solid-phase synthesis of oligoribonucleotides using the 2-dansylethoxycarbonyl (=2−{[5-(dimethylamino)naphthalen-l-yl]sulfonyl}ethoxycarbonyl; Dnseoc) group for 5′-hydroxy protection. ibid.1994,77, 988–998

4. a) van Boom, J.H.; Burgers, P.M.J. Use of levulinic acid in the protection of oligonucleotides via the modified phosphotriester method: synthesis of decaribonucleotide U-A-U-A-U-A-U-A-U-A. Tetrahedron Lett.1976, 4875–4878; b) van Boom, J.H.; Burgers, P.M.J.; Verdegaal, C.H.M.; Wille, S. Synthesis of oligonucleotides with sequences identical with or analogous to the 3′-end of 16S ribosomal RNA of Escherichia coli: preparation of U-C-C-U-U-A and A-C-C-U-C-C-U-U-A via the modified phosphotriester method. Tetrahedron1978,34, 1999–2007; c) Iwai, S.; Ohtsuka, E. 5′-Levulinyl and 2′-tetrahydrofuranyl protection for the synthesis of oligoribonucleotides by the phosphoramidite approach. Nucleic Acids Res.1988,16, 9443–9456; d) Iwai, S.; Sasaki, T.; Ohtsuka, E. Large scale synthesis of oligoribonucleotides on a solid support: synthesis of a catalytic RNA duplex. Tetrahedron1990,46, 6673–6688

5. a) van Boom, J.H.; Christodoulou, C.; Reese, C.B.; Sindona, G. Two new protected acyl protecting groups for alcoholic hydroxy functions. J. Chem. Soc., Perkin Trans. 11984, 1785–1790; b) Reese, C.B. The problem of 2′-protection in rapid oligoribonucleotide synthesis. Nucleosides Nucleotides1987,6, 121–129; c) Christodoulou, C.; Agrawal, S.; Gait, M. A new 5′-protecting group for use in solid-phase synthesis of oligoribonucleotides. ibid.1987,6, 341–344

Cited by 2 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. A Facile Synthesis of 1,1′-Spirobi(3H,3′H)isobenzofurans;Synthesis;2007-03

2. Levulinic Anhydride;Encyclopedia of Reagents for Organic Synthesis;2005-10-15

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