Nucleotide Analogues Containing the P-F Bond. An Overview of the Synthetic MethodsFootnote^a

This paper is dedicated to the late Professor Tsujiaki Hata

References

• Uhlmann , E. and Peyman , A. 1990 . Chem. Rev. , 90 : 543 – 584 .
   Web of Science ®Google Scholar
• Hanvey , J. C. , Peffer , N. J. , Bisi , J. E. , Thomson , S. A. , Cadilla , R. , Josey , J. A. , Ricca , D. J. , Hassman , C. F. , Bonham , M. A. , Au , K. G. , Carter , S. G. , Bruckenstein , D. A. , Boyd , A. L. , Noble , S. A. and Babiss , L. E. 1992 . Science , 258 : 1481 – 1485 .
   PubMed Web of Science ®Google Scholar
• Englisch , U. and Gauss , D. M. 1991 . Angew. Chem., Int. Ed. Engl. , 30 : 613 – 629 .
   Web of Science ®Google Scholar
• Cohen , J. S. 1992 . Trends Biotechnol. , 10 : 87 – 90 .
   PubMed Web of Science ®Google Scholar
• Cohen , J. S. 1989 . Trends Pharmacol. Sci. , 10 : 435 – 437 .
   PubMed Web of Science ®Google Scholar
• Stein , C. A. and Cohen , J. S. 1989 . Oligodeoxynucleotides-Antisense Inhibitors of Gene Expression , Edited by: Cohen , J. S. Vol. 12 , 97 – 117 . New York : The Macmillan Press Ltd. .
   Google Scholar
• Matulic-Adamic , J. , Rosenberg , I. , Arzumanov , A. A. , Dyatkina , N. B. , Shirokova , E. A. , Krayevsky , A. A. and Watanabe , K. A. 1993 . Nucleosides Nucleotides , 12 : 1085 – 1092 .
   Web of Science ®Google Scholar
• Dyatkina , N. , Arzumanov , A. , Krayevsky , A. , O'Hara , B. , Gluzman , Y. , Baron , P. , MacLow , C. and Polsky , B. 1994 . Nucleosides Nucleotides , 13 : 325 – 337 .
   Google Scholar
• Dabkowski , W. , Tworowska , I. , Michalski , J. and Cramer , F. 1995 . J. Chem. Soc. Chem. Commun. , : 1435 – 1436 .
   Google Scholar
• Dabkowski , W. , Cramer , F. and Michalski , J. 1993 . Phosphor. Sulfur Silicon , 75 : 91 – 94 .
   Web of Science ®Google Scholar
• Dabkowski , W. and Tworowska , I. 1995 . Chem. Lett. , : 727 – 728 .
   Web of Science ®Google Scholar
• Dabkowski , W. , Cramer , F. and Michalski , J. 1992 . J. Chem. Soc. Perkin Trans. , I : 1447 – 1452 .
   Google Scholar
• Michalski , J. , Dabkowski , W. , Lopusinski , A. and Cramer , F. 1991 . Nucleosides Nucleotides , 10 : 283 – 286 .
   Web of Science ®Google Scholar
• Misiura , K. , Pietrasiak , D. and Stec , W. J. 1995 . J. Chem. Soc. Chem. Commun. , : 613 – 614 .
   Google Scholar
• Bollmark , M. , Zain , R. and Stawinski , J. 1996 . Tetrahedron Lett. , 37 : 3537 – 3540 .
   Web of Science ®Google Scholar
• Bollmark , M. and Stawinski , J. 1996 . Tetrahedron Lett. , 37 : 5739 – 5742 .
   Web of Science ®Google Scholar
• Bollmark , M. and Stawinski , J. 1997 . Chem. Commun. , : 991 – 992 .
   Google Scholar
• Clark , J. H. 1980 . Chem. Rev. , 80 : 429 – 452 .
   Web of Science ®Google Scholar
• Zeffren , E. and Reavill , R. E. 1968 . Biochem. Biophys. Res. Commun. , 32 : 73 – 80 .
   Google Scholar
• Hood , A. and Lange , W. 1950 . J. Am. Chem. Soc. , 72 : 4956 – 4950 .
   Google Scholar
• Müller , E. , ed. 1964 . Methoden der organischen Chemie (Houben-Weyl) , vol. XII/2 , Stuttgart : George Thieme Verlag .
   Google Scholar
• Michalski , J. 1991 . Nucleic Acids Sym. Ser. , 24 : 79 – 82 .
   Google Scholar
• Lopusinski , A. and Michalski , J. 1982 . J. Am. Chem. Soc. , 104 : 290 – 291 .
   Google Scholar
• Dabkowski , W. , Cramer , F. and Michalski , J. 1988 . Tetrahedron Lett. , 29 : 3301 – 3302 .
   Web of Science ®Google Scholar
• Dabkowski , W. and Tworowska , I. 1995 . Tetrahedron Lett. , 36 : 1095 – 1098 .
   Web of Science ®Google Scholar
• Dabkowski , W. , Michalski , J. and Qing , W. 1990 . Angew. Chem., Int. Ed. Engl. , 29 : 522 – 523 .
   Google Scholar
• Dabkowski , W. , Cramer , F. and Michalski , J. 1987 . Tetrahedron Lett. , 28 : 3561 – 3562 .
   Web of Science ®Google Scholar
• Dabkowski , W. , Michalski , J. , Wasiak , J. and Cramer , F. 1994 . J. Chem. Soc. Perkin Trans. , 1 : 817 – 820 .
   Google Scholar
• Sund , C. and Chattopadhyaya , J. 1989 . Tetrahedron , 41 : 7523 – 7544 .
   Google Scholar
• Baraniak , J. , Stec , W. J. and Blackburn , G. M. 1995 . Tetrahedron Lett. , 36 : 8119 – 8122 .
   Google Scholar
• Dabkowski , W. and Michalski , J. 1995 . Polish J. Chem. , 69 : 979 – 980 .
   Google Scholar
• Garegg , P. J. , Regberg , T. , Stawinski , J. and Strömberg , R. 1985 . Chem. Scr. , 25 : 280 – 282 .
   Google Scholar
• Connolly , B. A. , Potter , B. V. L. , Eckstein , F. , Pingoud , A. and Grotjahn , L. 1984 . Biochemistry , 23 : 3443 – 3453 .
   PubMed Web of Science ®Google Scholar
• Stawinski , J. and Thelin , M. 1994 . J. Org. Chem. , 59 : 130 – 136 .
   Web of Science ®Google Scholar
• Wyrzykiewicz , T. W. and Cole , D. L. 1994 . Nucleic Acids Res. , 22 : 2667 – 2669 .
   PubMed Web of Science ®Google Scholar
• Eckstein , F. 1985 . Ann. Rev. Biochem. , 54 : 367 – 402 .
   PubMed Web of Science ®Google Scholar
• Beaucage , S. L. and Iyer , R. P. 1992 . Tetrahedron , 48 : 2223 – 2311 .
   Web of Science ®Google Scholar
• Stawinski , J. 1992 . Handbook of Organophosphorus Chemistry , Edited by: Engel , R. 377 – 434 . New York : Marcel Dekker .
   Google Scholar
• Stawinski , J. and Strömberg , R. 1993 . Trends Org. Chem. , 4 : 31 – 67 .
   Web of Science ®Google Scholar
• Bollmark , M. , Zain , R. and Stawinski , J. 1996 . Coll. Czech. Chem. Commun. (Special Issue) , 61 : S68 – 71 .
   Google Scholar
• Garegg , P. J. , Regberg , T. , Stawinski , J. and Strömberg , R. 1987 . J. Chem. Soc. Perkin Trans. , I : 1269 – 1273 .
   Google Scholar
• Atherton , F. R. , Openshaw , H. T. and Todd , A. R. 1945 . Chem. Soc. , : 660 – 663 .
   Web of Science ®Google Scholar
• Wittmann , R. 1963 . Chem. Ber. , 96 : 771 – 779 .
   Google Scholar
• Borden , R. K. and Smith , M. 1966 . J. Org. Chem. , 31 : 3241 – 3246 .
   Google Scholar
• Johnson , P. W. , von Tigerstrom , R. and Smith , M. 1975 . Nucleic Acids Res. , 2 : 1745 – 1749 .
   Google Scholar
• Watanabe , Y. , Sofue , S. , Ozaki , S. and Hirata , M. 1996 . Chem. Commun. , : 1815 – 1816 .
   Google Scholar
• Watanabe , Y. , Hyodo , N. and Ozaki , S. 1988 . Tetrahedron Lett. , 29 : 5763 – 5764 .
   Google Scholar
• Netherlands Patent 6,516,242 . July 28, 1966 .
   Google Scholar
• 1967 . CA , 66 : 11162j
   Google Scholar
• Jankowska , J. , Sobkowski , M. , Stawinski , J. and Kraszewski , A. 1994 . Tetrahedron Lett. , 35 : 3355 – 3358 .
   Web of Science ®Google Scholar
• Hata , T. and Sekine , M. 1974 . J. Am. Chem. Soc. , 96 : 7363 – 7364 .
   PubMed Web of Science ®Google Scholar
• Schönberg , A. 1935 . Chem. Ber. , 68 : 163 – 164 .
   Google Scholar
• Kamer , P. C. J. , Roelen , H. C. P. F. , van den Elst , H. , van der Marel , G. A. and van Boom , J. H. 1989 . Tetrahedron Lett. , 30 : 6757 – 6760 .
   Web of Science ®Google Scholar
• Stawinski , J. , Strömberg , R. and Zain , R. 1992 . Tetrahedron Lett. , 33 : 3185 – 3188 .
   Web of Science ®Google Scholar
• Stawinski , J. , Thelin , M. and Zain , R. 1989 . Tetrahedron Lett. , 30 : 2157 – 2160 .
   Web of Science ®Google Scholar
• Zain , R. and Stawinski , J. 1996 . J. Org. Chem. , 61 : 6617 – 6622 .
   PubMed Web of Science ®Google Scholar
• Brill , W. K.-D. , Nielsen , J. and Caruthers , M. 1991 . J. Am. Chem. Soc. , 113 : 3972 – 3980 .
   Web of Science ®Google Scholar
• Stawinski , J. and Thelin , M. 1991 . J. Org. Chem. , 56 : 5169 – 5175 .
   Web of Science ®Google Scholar
• Stawinski , J. and Thelin , M. 1992 . Tetrahedron Lett. , 33 : 7255 – 7258 .
   Web of Science ®Google Scholar
• Misiura , K. , Szymanowicz , D. and Stec , W. J. 1996 . Collect. Czech. Chem. Commun. (Special Issue) , 61 : S101 – S106 .
   Google Scholar
• Zain , R. , Strömberg , R. and Stawinski , J. 1995 . J. Org. Chem. , 60 : 8241 – 8244 .
   Web of Science ®Google Scholar
• Porritt , G. M. and Reese , C. B. 1989 . Tetrahedron Lett. , 30 : 4713 – 4716 .
   Web of Science ®Google Scholar
• Brill , W. K.-D. , Yau , E. K. and Caruthers , M. H. 1989 . Tetrahedron Lett. , 30 : 6621 – 6624 .
   Web of Science ®Google Scholar
• Stawinski , J. , Szabó , T. , Thelin , M. , Westman , E. and Zain , R. 1990 . Collect. Czech. Chem. Commun. , 55 : 141 – 144 .
   Google Scholar