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Volumn 17, Issue 10, 2012, Pages 12102-12120

Acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution

Author keywords

Cyclodextrin; Oligonucleotides; Phosphoramidites; Soluble support; Synthesis

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; OLIGODEOXYRIBONUCLEOTIDE;

EID: 84868097079     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171012102     Document Type: Article
Times cited : (22)

References (33)
  • 1
    • 0026606239 scopus 로고
    • Advances in the synthesis of oligonucleotides by the phosphoramidite approach
    • Beaucage, S.L.; Iyer, R.P. Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron 1992, 48, 2223-2311.
    • (1992) Tetrahedron , vol.48 , pp. 2223-2311
    • Beaucage, S.L.1    Iyer, R.P.2
  • 2
    • 0034757858 scopus 로고    scopus 로고
    • Toward an ideal synthesis of oligonucleotides: Development of a novel phosphoramidite method with high capability
    • Hayakawa, Y. Toward an ideal synthesis of oligonucleotides: Development of a novel phosphoramidite method with high capability. Bull. Chem. Soc. Jpn. 2001, 74, 1547-1565.
    • (2001) Bull. Chem. Soc. Jpn. , vol.74 , pp. 1547-1565
    • Hayakawa, Y.1
  • 3
    • 0034385487 scopus 로고    scopus 로고
    • Synthesis of antisense oligonucleotides: Replacement of 3H-1, 2-benzodithiol-3-one 1, 1-dioxide (Beaucage reagent) with phenylacetyl disulfide (PADS) as efficient sulfurization reagent: From bench to bulk manufacture of active pharmaceutical ingredient
    • Cheruvalleth, S.Z.; Carty, R.L.; Moore, M.H.; Capaldi, D.C.; Krotz, A.H.; Wheeler, P.D.; Turney, B.J.; Craig, S.R.; Gaus, H.J.; Scozzari, A.N.; et al. Synthesis of antisense oligonucleotides: Replacement of 3H-1, 2-benzodithiol-3-one 1, 1-dioxide (Beaucage reagent) with phenylacetyl disulfide (PADS) as efficient sulfurization reagent: From bench to bulk manufacture of active pharmaceutical ingredient. Org. Process Res. Dev. 2000, 4, 199-204.
    • (2000) Org. Process Res. Dev. , vol.4 , pp. 199-204
    • Cheruvalleth, S.Z.1    Carty, R.L.2    Moore, M.H.3    Capaldi, D.C.4    Krotz, A.H.5    Wheeler, P.D.6    Turney, B.J.7    Craig, S.R.8    Gaus, H.J.9    Scozzari, A.N.10
  • 4
    • 0034740932 scopus 로고    scopus 로고
    • Reusable solid-phase supports for oligonucleotides and antisense therapeutics
    • Pon, R.T.; Yu, S.; Guo, Z.; Deshmukh, R.; Sanghvi, Y.S. Reusable solid-phase supports for oligonucleotides and antisense therapeutics. J. Chem. Soc. Perkin Trans. 1 2001, 2638-2643.
    • (2001) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2638-2643
    • Pon, R.T.1    Yu, S.2    Guo, Z.3    Deshmukh, R.4    Sanghvi, Y.S.5
  • 5
    • 10444236381 scopus 로고    scopus 로고
    • Therapeutic oligonucleotides: The state-of-the-art in purification technologies
    • Sanghvi, Y.S.; Schulte, M. Therapeutic oligonucleotides: The state-of-the-art in purification technologies. Curr. Opin. Drug Discov. Dev. 2004, 6, 765-776.
    • (2004) Curr. Opin. Drug Discov. Dev. , vol.6 , pp. 765-776
    • Sanghvi, Y.S.1    Schulte, M.2
  • 6
    • 0029339276 scopus 로고
    • Large-scale oligonucleotide synthesizers. I. Basic principles and system design
    • Anderson, N.G.; Anderson, N.L.; Taylor, J.; Goodman, J. Large-scale oligonucleotide synthesizers. I. Basic principles and system design. Appl. Biochem. Biotechnol. 1995, 54, 19-42.
    • (1995) Appl. Biochem. Biotechnol. , vol.54 , pp. 19-42
    • Anderson, N.G.1    Anderson, N.L.2    Taylor, J.3    Goodman, J.4
  • 7
    • 0027153587 scopus 로고
    • Large scale, liquid phase synthesis of oligonucleotides by the phosphoramidite approach
    • Bonora, G.M.; Biancotto, G.; Maffini, M.; Scremin, C.L. Large scale, liquid phase synthesis of oligonucleotides by the phosphoramidite approach. Nucleic Acids Res. 1993, 21, 1213-1217.
    • (1993) Nucleic Acids Res. , vol.21 , pp. 1213-1217
    • Bonora, G.M.1    Biancotto, G.2    Maffini, M.3    Scremin, C.L.4
  • 8
    • 0027176594 scopus 로고
    • Liquid phase synthesis of phosphorothioate oligonucleotides on polyethylene glycol support
    • Scremin, C.L.; Bonora, G.M. Liquid phase synthesis of phosphorothioate oligonucleotides on polyethylene glycol support. Tetrahedron Lett. 1993, 29, 4663-4666.
    • (1993) Tetrahedron Lett. , vol.29 , pp. 4663-4666
    • Scremin, C.L.1    Bonora, G.M.2
  • 9
    • 51249161487 scopus 로고
    • Polyethylene-glycol\A high-efficiency liquid-phase (HELP) for the large-scale synthesis of oligonucleotides
    • Bonora, G.M. Polyethylene-glycol\A high-efficiency liquid-phase (HELP) for the large-scale synthesis of oligonucleotides. Appl. Biochem. Biotechnol. 1995, 54, 3-17.
    • (1995) Appl. Biochem. Biotechnol. , vol.54 , pp. 3-17
    • Bonora, G.M.1
  • 11
    • 0034803833 scopus 로고    scopus 로고
    • Triple MPEG-conjugated helix-forming oligonucleotides (TRIPEGXs): Liquid-phase synthesis of natural and chimeric "all-purine" sequences linked to high molecular weight poly(ethylene glycols)
    • Ballico, M.; Drioli, S.; Morvan, F.; Xodo, L.; Bonora, G.M. Triple, MPEG-conjugated, helix-forming oligonucleotides (TRIPEGXs): Liquid-phase synthesis of natural and chimeric "All-purine" sequences linked to high molecular weight poly(ethylene glycols). Bioconjug. Chem. 2001, 12, 719-725.
    • (2001) Bioconjug. Chem. , vol.12 , pp. 719-725
    • Ballico, M.1    Drioli, S.2    Morvan, F.3    Xodo, L.4    Bonora, G.M.5
  • 12
    • 0034005228 scopus 로고    scopus 로고
    • Large Scale, Liquid phase oligonucleotide synthesis by alkyl H-phosphonate approach
    • Padiya, K.J.; Salunkhe, M.M. Large Scale, Liquid phase oligonucleotide synthesis by alkyl H-phosphonate approach. Bioorg. Med. Chem. 2000, 8, 337-342.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 337-342
    • Padiya, K.J.1    Salunkhe, M.M.2
  • 13
    • 0025354607 scopus 로고
    • HELP (high efficiency liquid phase) new oligonucleotide synthesis on soluble polymeric support
    • Bonora, G.M.; Scremin, C.L.; Colonna, F.P.; Garbesi, A. HELP (high efficiency liquid phase) new oligonucleotide synthesis on soluble polymeric support. Nucleic Acids Res. 1990, 18, 3155-3159.
    • (1990) Nucleic Acids Res. , vol.18 , pp. 3155-3159
    • Bonora, G.M.1    Scremin, C.L.2    Colonna, F.P.3    Garbesi, A.4
  • 14
    • 0025805929 scopus 로고
    • Large scale H.E.L.P. synthesis of oligodeoxynucleotides by the hydroxybenzotriazole phosphotriester approach
    • Colonna, F.P.; Scremin, C.L.; Bonora, G.M. Large scale H.E.L.P. synthesis of oligodeoxynucleotides by the hydroxybenzotriazole phosphotriester approach. Tetrahedron Lett. 1991, 32, 3251-3254.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3251-3254
    • Colonna, F.P.1    Scremin, C.L.2    Bonora, G.M.3
  • 16
    • 33749130643 scopus 로고    scopus 로고
    • A novel approach to oligonucleotide synthesis using an imidazolium ion tag as a soluble support
    • Donga, R.A.; Khaliq-Uz-Zaman, S.M.; Chan, T.-H.; Damha, M.J. A novel approach to oligonucleotide synthesis using an imidazolium ion tag as a soluble support. J. Org. Chem. 2006, 71, 7907-7910.
    • (2006) J. Org. Chem. , vol.71 , pp. 7907-7910
    • Donga, R.A.1    Khaliq-Uz-Zaman, S.M.2    Chan, T.-H.3    Damha, M.J.4
  • 19
    • 70349142256 scopus 로고    scopus 로고
    • Efficient guest inclusion by β-cyclodextrin attached to the ends of DNA oligomers upon hybridization to various DNA conjugates
    • Kuzuya, A.; Ohnishi, T.; Wasano, T.; Nagaoka, S.; Sumaoka, J.; Ihara, T.; Jyo, A.; Komiyama, M. Efficient guest inclusion by β-cyclodextrin attached to the ends of DNA oligomers upon hybridization to various DNA conjugates. Bioconjug Chem. 2009, 20, 1643-1649.
    • (2009) Bioconjug Chem. , vol.20 , pp. 1643-1649
    • Kuzuya, A.1    Ohnishi, T.2    Wasano, T.3    Nagaoka, S.4    Sumaoka, J.5    Ihara, T.6    Jyo, A.7    Komiyama, M.8
  • 22
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem. Int. Ed. Engl. 2002, 41, 2596-2599.
    • (2002) Angew. Chem. Int. Ed. Engl. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 23
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2, 3]-Triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides
    • Tornoe, C.W.; Christensen, C; Meldal, M. Peptidotriazoles on solid phase: [1, 2, 3]-Triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 24
    • 0000860264 scopus 로고
    • The tert-butyldimethylsilyl group as a protecting group in deoxynucleosides
    • Ogilvie, K.K. The tert-butyldimethylsilyl group as a protecting group in deoxynucleosides. Can. J. Chem. 1973, 51, 3799-3807.
    • (1973) Can. J. Chem. , vol.51 , pp. 3799-3807
    • Ogilvie, K.K.1
  • 25
    • 49549116663 scopus 로고    scopus 로고
    • Protecting group transfer: Unusual method of removal of Tr and TBDMS groups by transetherification
    • Cabral, N.L.D.; Hoeltgebaum Thiessen, L.J.; Doboszwski, B. Protecting group transfer: Unusual method of removal of Tr and TBDMS groups by transetherification. Nucleos. Nucleot. Nucleic Acids 2008, 27, 931-948.
    • (2008) Nucleos. Nucleot. Nucleic Acids , vol.27 , pp. 931-948
    • Cabral, N.L.D.1    Hoeltgebaum Thiessen, L.J.2    Doboszwski, B.3
  • 26
    • 4544337310 scopus 로고    scopus 로고
    • A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers
    • Khan, A.T.; Ghosh, S.; Choudhury, L.H. A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers. Eur. J. Org. Chem. 2004, 2198-2204.
    • (2004) Eur. J. Org. Chem. , pp. 2198-2204
    • Khan, A.T.1    Ghosh, S.2    Choudhury, L.H.3
  • 27
    • 2442720851 scopus 로고    scopus 로고
    • A facile solid-phase synthesis of oligonucleotides containing a 3'-3' phosphodiester bond for alternate strand triple-helix formation
    • De Napoli, L.; Di Fabio, G; Messere, A.; Montesarchio, D.; Piccialli, G; Varra, M. A facile solid-phase synthesis of oligonucleotides containing a 3'-3' phosphodiester bond for alternate strand triple-helix formation. Eur. J. Org. Chem. 1998, 2119-2125.
    • (1998) Eur. J. Org. Chem. , pp. 2119-2125
    • De Napoli, L.1    Di Fabio, G.2    Messere, A.3    Montesarchio, D.4    Piccialli, G.5    Varra, M.6
  • 28
    • 0033614990 scopus 로고    scopus 로고
    • Nucleosides and Nucleotides 185. Synthesis and biological activities of 4'a-C-branched chain sugar pyrimidine nucleosides
    • Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matsuda, A. Nucleosides and Nucleotides 185. Synthesis and biological activities of 4'a-C-branched chain sugar pyrimidine nucleosides. J. Med. Chem. 1999, 42, 2901-2908.
    • (1999) J. Med. Chem. , vol.42 , pp. 2901-2908
    • Nomura, M.1    Shuto, S.2    Tanaka, M.3    Sasaki, T.4    Mori, S.5    Shigeta, S.6    Matsuda, A.7
  • 30
    • 0034641284 scopus 로고    scopus 로고
    • Minor groove hydration is critical to the stability of DNA duplexes
    • Lan, T.; McLaughlin, L.W. Minor groove hydration is critical to the stability of DNA duplexes. J. Am. Chem. Soc. 2000, 122, 6512-6513.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6512-6513
    • Lan, T.1    McLaughlin, L.W.2
  • 31
    • 33845955004 scopus 로고    scopus 로고
    • Heterogeneous diazo-transfer reaction: A facile unmasking of azide groups on amine-functionalized insoluble supports for solid phase synthesis
    • Oyelere, A.K.; Chen, P.C.; Yao, L.P.; Boguslavsky, N. Heterogeneous diazo-transfer reaction: A facile unmasking of azide groups on amine-functionalized insoluble supports for solid phase synthesis, J. Org. Chem. 2006, 71, 9791-9796.
    • (2006) J. Org. Chem. , vol.71 , pp. 9791-9796
    • Oyelere, A.K.1    Chen, P.C.2    Yao, L.P.3    Boguslavsky, N.4
  • 33
    • 70349506772 scopus 로고    scopus 로고
    • Preparation and characterization of a water soluble methylated β-cyclodextrin/camphorquinone complex
    • Zhang, J.; Xiao, P.; Shi, S.; Nie, J. Preparation and characterization of a water soluble methylated β-cyclodextrin/camphorquinone complex. Polym. Adv. Technol. 2009, 20, 723-728.
    • (2009) Polym. Adv. Technol. , vol.20 , pp. 723-728
    • Zhang, J.1    Xiao, P.2    Shi, S.3    Nie, J.4


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