A Novel Universal Linker for Efficient Synthesis of Phosphorothioate Oligonucleotides

REFERENCES AND NOTES

• Beaucage , S. L. and Iyer , R. P. 1992 . Advances in the synthesis of oligonucleotides by the phosphoramidite Approach . Tetrahedron , 48 : 2223 – 2311 .
   Web of Science ®Google Scholar
• Beaucage , S. L. and Iyer , R. P. 1993 . Phosphoramidite derivatives and their synthetic applications . Tetrahedron , 49 : 1925 – 1963 .
   Web of Science ®Google Scholar
• Beaucage , S. L. 1999 . “ Oligonucleotide synthesis ” . In Comprehensive Natural Product Chemistry , Edited by: Barton , S. , D. , H. R. and Nakanishi , K. Vol. 105 , New York : Pergamon Press . [in Volume 7.05: DNA and Aspects of Molecular Biology, series ed., Kool, E.T.]
   Google Scholar
• Gough , G.R. , Brunden , M. J. and Gilham , P.T. 1983 . 2′(3′)-O-Benzoyluridine 5′ linked to glass: An all-purpose support for solid-phase synthesis of oligodeoxyribonucleotides . Tetrahedron Lett. , 24 : 5321 – 5324 .
   Web of Science ®Google Scholar
• de Bear , J. S. , Hayes , J. A. , Koleck , M. P. and Gough , G. R. 1987 . A universal glass support for oligodeoxyribonucleotide synthesis . Nucleosides Nucleotides , 6 : 821 – 830 .
   Google Scholar
• Schwartz , M. E. , Breaker , R. R. , Asteriadis , G. T. and Gough , G. R. 1995 . A universal adaptor for chemical synthesis of DNA or RNA on any single type of solid support . Tetrahedron Lett , 36 : 27 – 30 .
   Web of Science ®Google Scholar
• Lyttle , M. H. , Hudson , D. and Cook , R. M. 1996 . A new universal linker for solid phase DNA synthesis . Nucleic Acids Res , 24 : 2793 – 2798 .
   PubMed Web of Science ®Google Scholar
• Lyttle , M. H. , Dick , D. J. , Hudson , D. and Cook , R. M. 1999 . A phosphate bound universal linker for DNA synthesis . Nucleosides Nucleotides , 18 : 1809 – 1824 .
   PubMed Web of Science ®Google Scholar
• Scheuer-Larsen , C. , Rosenbohm , C. , Joergensen , T.J. D. and Wengel , J. 1997 . Introduction of a universal solid support for oligonucleotide synthesis . Nucleosides Nucleotides , 16 : 67 – 80 .
   Google Scholar
• Kumar , P. and Gupta , K. C. 1999 . Rapid conditions for the cleavage of oligodeoxyribonucleotides from cis-diol-bearing universal polymer supports and their deprotection. . Nucleic Acids Res. , 27 : e2
   PubMedGoogle Scholar
• Nelson , P. S. , Muthini , S. , Vierra , M. , Acosta , L. and Smith , T. H. 1997 . Rainbow Universal CPG: A versatile solid support for oligonucleotide synthesis . Biotechniques , 22 : 752 – 756 .
   PubMed Web of Science ®Google Scholar
• Kumar , P. , Mahajan , S. and Gupta , K. C. 2004 . Universal reusable polymer support for oligonucleotide synthesis. . J. Org. Chem. , 69 : 6482 – 6485 .
   PubMed Web of Science ®Google Scholar
• Kumar , P. and Gupta , K. C. 1999 . Novel conditions for rapid and clean deprotection of oligodeoxyribonucleotides from universal polymer supports. . Reac. Funct. Polym. , 41 : 197 – 204 .
   Web of Science ®Google Scholar
• Azhayev , A. V. 1999 . A new universl solid support for oligonucleotide synthesis. . Tetrahedron , 55 : 787 – 800 .
   Web of Science ®Google Scholar
• Kumar , P. and Gupta , K. C. 2003 . Rapid cleavage of oligodeoxyribonucleotides from cis-diol bearing universal polymer support. . Helv. Chim. Acta , 86 : 59 – 64 .
   Web of Science ®Google Scholar
• Kumar , P. , Dhawan , R. , Chandra , R. and Gupta , K. C. 2002 . Polyamine-assisted rapid and clean cleavage of oligonucleotides from cis-diol bearing universal support. . Nucleic Acids Res. , 30 : e130
   PubMed Web of Science ®Google Scholar
• Scheuer-Larson , C. , Rosenbohm , C. , Jorgensen , T.J. D. and Wengel , J. 1997 . Introduction of a universal support for oligonucleotide synthesis. . Nucleosides Nucleotides , 16 : 67 – 80 .
   Google Scholar
• Nelson , P. S. , Muthini , S. , Kent , M. A. and Smith , T. H. 1997 . Rainbow universal CPG: A versatile solid support for oligodeoxyribonucleotide preparation . Nucleosides Nucleotides , 16 : 1951 – 1959 .
   Google Scholar
• Azhayev , A. V. and Antopolsky , M. L. 2001 . Amide group assisted 3′-dephosphorylation of oligonucleotides synthesized on universal supports. . Tetrahedron , 57 : 4977 – 4986 .
   Web of Science ®Google Scholar
• Zheng , X. , Gaffney , B. L. and Jones , R. A. 1997 . RNA synthesis using a universal, base-stable allyl linker. . Nucleic Acids Res. , 25 : 3980 – 3983 .
   PubMed Web of Science ®Google Scholar
• Guzaev , A. P. and Manoharan , M. 2003 . A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. . J. Am. Chem. Soc. , 125 : 2380 – 2381 .
   PubMed Web of Science ®Google Scholar
• Krishna , Kumar R. , Guzaev , A. P. , Rentel , C. and Ravikumar , V. T. 2006 . Efficient synthesis of antisense phosphorothioate oligonucleotides using a universal solid support. . Tetrahedron , 62 : 4528 – 4534 .
   Google Scholar
• Daniels , R. and Fischer , J. L. 1963 . The osmium tetroxide-catalyzed hydroxylation of furan-maleic anhydride adduct. . J. Org. Chem. , 28 : 320 – 322 .
   Web of Science ®Google Scholar
• Neubert , B. J. and Snider , B. B. 2003 . Synthesis of (±)-Phloeodictine A1. . Org. Lett. , 5 : 765 – 768 .
   PubMed Web of Science ®Google Scholar
• Corrie , J.E. T. and Munasinghe , V.R. N. 2003 . Reaction of amino acids with exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride forms hemi-maleate salts, not maleimides. . ARKIVOC , : 69 – 72 .
   Web of Science ®Google Scholar
• Lee , N. -J. , Kang , N. -I. , Cho , W. -J. , Kim , S. -H. , Kang , K. -T. and Theodorakis , E. A. 2001 . Synthesis and biological activity of medium range molecular weight polymers containing exo-3,6-epoxy-1,2,3,6-tetrahydrophthalimidocaproic acid. . Polym. Int. , 50 : 1010 – 1015 .
   Web of Science ®Google Scholar
• “ Experience has taught us that yields expressed in terms of weight/μmol of support are more reliable than those expressed in terms of optical density/μmol. ” .
   Google Scholar
• Capaldi , D. C. , Gaus , H. , Krotz , A. H. , Arnold , J. , Carty , R. L. , Moore , M. N. , Scozzari , A. N. , Lowery , K. , Cole , D. L. and Ravikumar , V. T. 2003 . Synthesis of high-quality antisense drugs. Addition of acrylonitrile to phosphorothioate oligonucleotides: Adduct characterization and avoidance. . Org. Proc. Res. & Dev. , 7 : 832 – 838 .
   Web of Science ®Google Scholar
• Umemoto , T. and Wada , T. 2005 . Nitromethane as a scavenger of acrylonitrile in the deprotection of synthetic oligonucleotides. . Tetrahedron Lett. , 46 : 4251 – 4253 .
   Web of Science ®Google Scholar
• Krotz , A. H. , Cole , D. L. and Ravikumar , V. T. 1999 . Synthesis of an antisense oligonucleotide targeted against C-raf kinase: Efficient oligonucleotide synthesis without chlorinated solvents. . Bioorg. Med. Chem. , 7 : 435 – 439 .
   PubMed Web of Science ®Google Scholar
• Krotz , A. H. , Carty , R. L. , Moore , M. N. , Scozzari , A. N. , Cole , D. L. and Ravikumar , V. T. 1999 . Synthesis of antisense oligonucleotides using environmentally friendly and safe deprotection procedures. . Green Chem. , : 277 – 281 .
   Web of Science ®Google Scholar
• Wang , Z. , Siwkowski , A. , Lima , W. F. , Olsen , P. and Ravikumar , V. T. 2006 . Antisense oligonucleotides: Efficient synthesis of 2′-O-methoxyethyl phosphorothioate oligonucleotides using 4,5-dicyanoimidazole. Are these oligonucleotides comparable to those synthesized using 1 H-tetrazole as coupling activators? . Bioorg. Med. Chem. , 14 : 5049 – 5060 .
   PubMed Web of Science ®Google Scholar
• Vargeese , C. , Carter , J. , Yegge , J. , Krivjansky , S. , Settle , A. , Kropp , E. , Peterson , K. and Pieken , W. 1998 . Efficient activation of nucleoside phosphoramidites with 4,5-dicyanoimidazole during oligonucleotide synthesis. . Nucleic Acids Res. , 26 : 1046 – 1050 .
   PubMed Web of Science ®Google Scholar
• Capaldi , D. C. , Scozzari , A. N. , Cole , D. L. and Ravikumar , V. T. 1999 . Is it essential to use anhydrous acetonitrile in the manufacture of phosphorothioate oligonucleotides? . Org. Proc. Res. & Dev. , 3 : 485 – 487 .
   Web of Science ®Google Scholar
• Cheruvallath , Z. S. , Wheeler , P. D. , Cole , D. L. and Ravikumar , V. T. 1999 . Use of phenylacetyl disulfide (PADS) in the synthesis of oligodeoxyribonucleotide phosphorothioates. . Nucleosides Nucleotides , 18 : 485 – 492 .
   Google Scholar
• Cheruvallath , Z. S. , Carty , R. L. , Moore , M. N. , Capaldi , D. C. , Krotz , A. H. , Wheeler , P. D. , Turney , B. J. , Craig , S. R. , Gaus , H. J. , Scozzari , A. N. , Cole , D. L. and Ravikumar , V. T. 2000 . Synthesis of antisense oligonucleotides: Replacement of 3 H-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. Proc. Res. & Dev. , 4 : 199 – 204 .
   Web of Science ®Google Scholar
• Krotz , A. H. , Gorman , D. , Mataruse , P. , Foster , C. , Godbout , J. D. , Coffin , C. C. and Scozzari , A. N. 2004 . Phosphorothioate oligonucleotides with low phosphate diester content: Greater than 99.9% sulfurization efficiency with “aged” solutions of phenylacetyl disulfide (PADS). . Org. Proc. Res. & Dev. , 8 : 852 – 858 .
   Web of Science ®Google Scholar