Oligonucleotides containing a nucleotide analog with an ethynylfluorobenzene as nucleobase surrogate

Tetrahedron Letters

Volumn 43, Issue 48, 2002, Pages 8755-8758

  Griesang, Niels ^a   Richert, Clemens ^a,b  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Base pairing; C nucleosides; Oligonucleotides

Indexed keywords

1 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 2 ETHYNYL 4 FLUOROBENZENE; BENZENE DERIVATIVE; DIFLUOROTOLUENE; NUCLEIC ACID BASE; NUCLEOTIDE DERIVATIVE; OLIGONUCLEOTIDE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NUCLEOTIDE METABOLISM; SYNTHESIS;

EID: 0037175490     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02153-6     Document Type: Article

References (47)

1. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
2. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
3. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
4. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
5. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
6. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
7. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
8. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
9. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
10. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
11. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
12. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
13. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
14. Selected references: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238-7242; (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863-1872; (c) Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671-7678; (d) Guckian, K.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183; (e) Moran, S.; Ren, R. X.-F.; Rumney, S.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057; (f) Morales, J. C.; Kool, E. T. Nature Struc. Biol. 1998, 5, 950-954; (g) Matray, T. J.; Kool, E. T. J. Am. Chem. Soc. 1998, 120, 6191-6192; (h) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324; (i) Kool, E. T. Ann. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22; (j) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586; (k) Ogawa, A. K.; Wu, Y.; McMinn, D. L. Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287; (l) Tae, E. J.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440; (m) Parsch, J.; Engels, J. W. Helv. Chim. Acta 2000, 83, 1791-1808; (n) Seela, F.; Bourgeois, W.; Rosemeyer, H.; Wenzel, T. Helv. Chim. Acta 1996, 79, 488-498.
15. Selected references: (a) Moran, S.; Ren, R. X.-F.; Kool, E.T. Proc. Natl. Acad. Sci. USA 1997, 94, 10506-10511; (b) Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847; (c) Cubero, E.; Sherer, E. C.; Luque, F. J.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 8653-8654.
16. Selected references: (a) Moran, S.; Ren, R. X.-F.; Kool, E.T. Proc. Natl. Acad. Sci. USA 1997, 94, 10506-10511; (b) Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847; (c) Cubero, E.; Sherer, E. C.; Luque, F. J.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 8653-8654.
17. Selected references: (a) Moran, S.; Ren, R. X.-F.; Kool, E.T. Proc. Natl. Acad. Sci. USA 1997, 94, 10506-10511; (b) Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847; (c) Cubero, E.; Sherer, E. C.; Luque, F. J.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 1999, 121, 8653-8654.
18. For recent reviews, see e.g.: (a) Herdewijn, P. Antisense Nucleic Acid Drug Dev. 2000, 10, 297-310; (b) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1012, Angew. Chem. 2000, 112, 1046-1068.
19. For recent reviews, see e.g.: (a) Herdewijn, P. Antisense Nucleic Acid Drug Dev. 2000, 10, 297-310; (b) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1012, Angew. Chem. 2000, 112, 1046-1068.
20. For recent reviews, see e.g.: (a) Herdewijn, P. Antisense Nucleic Acid Drug Dev. 2000, 10, 297-310; (b) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1012, Angew. Chem. 2000, 112, 1046-1068.
21. Selected references: (a) Groebke, K.; Hunziker, J.; Fraser, W.; Peng, L.; Diederichsen, U.; Zimmermann, K.; Holzner, A. Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474; (b) Fidanza, J. A.; McGall, G. H. Nucleosides Nucleotides 1999, 18, 1293-1295; (c) Nguyen, H.-K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498; (d) Seela, F.; Becher, G. Nucleic Acids Res. 2001, 29, 2069-2078; (e) Okamoto, A.; Tanaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 97-99.
22. Selected references: (a) Groebke, K.; Hunziker, J.; Fraser, W.; Peng, L.; Diederichsen, U.; Zimmermann, K.; Holzner, A. Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474; (b) Fidanza, J. A.; McGall, G. H. Nucleosides Nucleotides 1999, 18, 1293-1295; (c) Nguyen, H.-K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498; (d) Seela, F.; Becher, G. Nucleic Acids Res. 2001, 29, 2069-2078; (e) Okamoto, A.; Tanaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 97-99.
23. Selected references: (a) Groebke, K.; Hunziker, J.; Fraser, W.; Peng, L.; Diederichsen, U.; Zimmermann, K.; Holzner, A. Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474; (b) Fidanza, J. A.; McGall, G. H. Nucleosides Nucleotides 1999, 18, 1293-1295; (c) Nguyen, H.-K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498; (d) Seela, F.; Becher, G. Nucleic Acids Res. 2001, 29, 2069-2078; (e) Okamoto, A.; Tanaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 97-99.
24. Selected references: (a) Groebke, K.; Hunziker, J.; Fraser, W.; Peng, L.; Diederichsen, U.; Zimmermann, K.; Holzner, A. Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474; (b) Fidanza, J. A.; McGall, G. H. Nucleosides Nucleotides 1999, 18, 1293-1295; (c) Nguyen, H.-K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498; (d) Seela, F.; Becher, G. Nucleic Acids Res. 2001, 29, 2069-2078; (e) Okamoto, A.; Tanaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 97-99.
25. Selected references: (a) Groebke, K.; Hunziker, J.; Fraser, W.; Peng, L.; Diederichsen, U.; Zimmermann, K.; Holzner, A. Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474; (b) Fidanza, J. A.; McGall, G. H. Nucleosides Nucleotides 1999, 18, 1293-1295; (c) Nguyen, H.-K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498; (d) Seela, F.; Becher, G. Nucleic Acids Res. 2001, 29, 2069-2078; (e) Okamoto, A.; Tanaka, K.; Saito, I. Bioorg. Med. Chem. Lett. 2002, 12, 97-99.
26. Lin K.-Y., Matteucci M.D. J. Am. Chem. Soc. 120:1998;8531-8532.
27. Wagner R.W., Matteucci M.D., Grant D., Huang T., Froehler B.C. Nature Biotechn. 14:1996;840-844.
28. Barnes T.W., Turner D.H. J. Am. Chem. Soc. 123:2001;4107-4118. and references cited therein.
29. Available from ABCR GmbH, D-76151 Karlsruhe, Germany.
30. Heaney, H.; Millar, I. T. Org. Syn. Collective Vol. V, 1120-1123.
31. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 50:1975;4467-4470.
32. Model protocol for a related substrate: Van Meurs, P. J.; Janssen, R. A. J. J. Org. Chem. 2000, 65, 5712-5719.
33. 3, 250 MHz) δ (ppm)=7.50 (dd, J=5.19, 8.8 Hz, 1H), 7.19 (dd, J=3.0, 8.8 Hz, 1H), 6.89 (ddd, J=3.0, 7.9, 8.8 Hz, 1H), 0.28 (s, 9H); Anal. calc: C 48.72; H 4.46, found C 48.48; H 4.42.
34. Chaudhuri N.C., Kool E.T. Tetrahedron Lett. 36:1995;1795-1798.
35. Fox J.J., Yung N.C., Wempen I., Hoffer M. J. Am. Chem. Soc. 83:1961;4066-4068.
36. Hoffer M. Chem. Ber. 23:1969;2777-2779.
37. Wang Z.X., Duan W., Wiebe L.I., Balzarini J., De Clerq E., Knaus E.E. Nucleosides Nucleotides Nucl. Acids. 20:2001;11-40.
38. 2) 0.65; EI-MS (70 eV) 584, 428, 139, 111.
39. 3) δ 114.6; EI-MS (70 eV) 512, 139, 111.
40. Anomers were assigned based on the results of ROESY experiments, where a H1′ to H4′ cross peak was observed for the β-anomer, but was absent for the α-anomer, and by comparison of coupling constants and chemical shifts of non-exchangeable deoxyribose resonances with those of reference C-nucleosides known from the literature: (a) Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341-347; (b) Ref. 13c.
41. Anomers were assigned based on the results of ROESY experiments, where a H1′ to H4′ cross peak was observed for the β-anomer, but was absent for the α-anomer, and by comparison of coupling constants and chemical shifts of non-exchangeable deoxyribose resonances with those of reference C-nucleosides known from the literature: (a) Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341-347; (b) Ref. 13c.
42. Kierzek R., Kopp D.W., Edmonds M., Caruthers M.H. Nucleic Acids Res. 14:1986;4751-4764.
43. Oligonucleotides were synthesized on an ABI 381 DNA synthesizer on a 1.0 μmolar scale, system software version 1.5. Total yields for modified oligonucleotides were within a factor of three of unmodified control strands prepared under the same conditions.
44. 9 ([M-H]-) calc: 3010.1, found 3007.5.
45. Different values have been published. In Ref. 1b, the melting point is given as 21.4°C. In the erratum (J. Am. Chem. Soc. 1996, 118, 931) the authors state that α-and β-anomers give little change in results. In 1997 (Ref.2a), the melting point is given as 27.4°C, whereas in 2000 (Ref. 3b), the authors again cite the earlier results (Ref. 1b), i.e. a melting point of 21.4°C and a ΔTm of 18.0°C. The melting point of control duplex CTTTTCTTTCTT:AAGAAAGAAAAG at 5 μM strand concentration and identical buffer conditions is given as 39.8°C in Guckian, K. M.; Morales, J. C.; Kool, E. T. J. Org. Chem. 1998, 63, 9652-9656 and as 43.2°C in Ref. 1g. In any case, the melting point for 8 with its complement is higher than either of the melting points reported for the duplex containing difluorotoluene.
46. See e.g.: (a) Dzantiev, L.; Alekseyev, Y. O.; Morales, J. C.; Kool, E. T.; Romano, L. J. Biochemistry 2001, 40, 3215-3221; (b) Kool, E. T. Curr. Opin. Chem. Biol. 2000, 4, 602-608 and Refs 1j and 1k.
47. See e.g.: (a) Dzantiev, L.; Alekseyev, Y. O.; Morales, J. C.; Kool, E. T.; Romano, L. J. Biochemistry 2001, 40, 3215-3221; (b) Kool, E. T. Curr. Opin. Chem. Biol. 2000, 4, 602-608 and Refs 1j and 1k.