Skip to main content

Abstract

In this chapter the chemical methods for gaining access to L-nucleosides, one of the most exciting and promising new directions of research in the field, will be presented. Aspects of the biological activity of these com- pounds, which differ from the natural series only in the configuration of the stereocentre at the 4-position of the sugar, will be mentioned briefly but dealt with in more detail in the following chapter.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. (a) Belleau, B., Dixit, D., Nguyen-Ga, N., Kraus, J. L. International Conferences on AIDS, Montreal, Canada, June 4-9 1990, paper no T.C.O.L. (b) Norbeck, D. W., Spanton, S., Broder, S., Mitsuya, H. Tetrahedron Lett. 1989, 30, 6263. (c) Soudeyns, H., Yao, X.-J., Gao, Q. et al. Antimicrob. Agents Chemother. 1991, 35, 1386.

    Google Scholar 

  2. (a) Votruba, L, Holy, A., Sorm, F. FEBS Lett. 1971, 19. (b) Holy, A., Sorm, F. Collect. Czech., Chem. Commun. 1971, 36, 3282.

    Google Scholar 

  3. Doskoccil, J., Holy, A. Nucleic Acids Res. 1974, 1, 491.

    Article  Google Scholar 

  4. Fucik, V., Kloudova, A., Holy, A. Nucleic Acids Res. 1974,1, 639.

    Article  CAS  Google Scholar 

  5. Simuth, J., Holy, A. Nucleic Acids Res. Spec. Publ. No.1 1975, s165.

    Google Scholar 

  6. (a) Jurovicik, M., Holy, A. Nucleic Acids. Res. 1976, 3, 2143. (b) Spadari, S., Maga, G., Focher, F. et al. J. Med. Chem. 1992, 35, 4214.

    Google Scholar 

  7. Schinazi, R. F., Chu, C. K., Peck, A. et al. Antimicrob. Agents Chemother. 1992, 36, 672.

    Article  CAS  Google Scholar 

  8. Coates, J. A. V., Cammack, N., Jenkinson, H. et al. Antimicrob. Agents Chemother. 1992, 36, 202.

    Article  CAS  Google Scholar 

  9. Coates, J. A. V., Cammack, N., Jenkinson, H. et al. Antimicrob. Agents Chemother. 1992, 36, 733.

    Article  CAS  Google Scholar 

  10. Doong, S.-L., Tsai, C H., Schinazi, R. F. et al. Proc. Natl. Acad. Sci. USA 1991, 88, 8495.

    Article  CAS  Google Scholar 

  11. Schinazi, R. F., McMillan, A., Cannon, D. et al. Antimicrob. Agents Chemother. 1992, 36, 2423.

    Article  CAS  Google Scholar 

  12. Beach, J. W., Jeong, L. S., Alves, A. J. et al. J. Org. Chem. 1992, 57, 2217.

    Article  CAS  Google Scholar 

  13. Furman, P. A., Davis, M., Liotta, D. C. et al. Antimicrob. Agents Chemother. 1992, 36, 2686.

    Article  CAS  Google Scholar 

  14. (a) Moyle, G. Exp. Opin. Invest. Drugs 1996, 5, 913. (b) Doran, C. M. Ann. Pharmacother. 1997, 31, 228.

    Article  CAS  Google Scholar 

  15. Robins, M., Jones, R., Mengel, R. J. Am. Chem. Soc. 1976, 98, 8213.

    Article  CAS  Google Scholar 

  16. Farina, V., Benigni, D. Tetrahedron Lett. 1988, 29, 1239.

    Article  CAS  Google Scholar 

  17. Okabe, M., Sun, R. C., Tam, S. Y. K. et al. J. Org. Chem. 1988, 53, 4780.

    Article  CAS  Google Scholar 

  18. Lin, T.-S., Luo, M.-Z., Liu, M.-C. et al. J. Med. Chem. 1994, 37, 798.

    Article  CAS  Google Scholar 

  19. Taniguchi, M., Koga, K., Yamada, S. Tetrahedron 1974, 30, 3547.

    Article  CAS  Google Scholar 

  20. Lin, T.-S., Luo, M.-Z., Liu, M.-C. et al. Nucleosides Nucleotides 1995,14, 1759.

    Article  CAS  Google Scholar 

  21. Lin, T.-S., Luo, M.-Z., Liu, M.-C. et al. Biochem. Pharmacol. 1994, 47, 171.

    CAS  Google Scholar 

  22. Lin, T.-S., Luo, M.-Z., Liu, M.-C. Tetrahedron Lett. 1994, 35, 3477.

    Article  CAS  Google Scholar 

  23. Lin, T.-S., Luo, M.-Z., Liu, M.-C. Nucleosides Nucleotides 1994,13, 1861.

    Article  CAS  Google Scholar 

  24. Lin, T-S., Guo, X., Luo, M.-Z. et al. Nucleosides Nucleotides 1995,14, 619.

    Article  CAS  Google Scholar 

  25. Lin, T.-S., Luo, M. Z., Liu, M. C Tetrahedron 1995, 51, 1055.

    Google Scholar 

  26. Mansuri, M. M., Farina, V., Starrett, J. E. et al. Bioorg. Med. Chem. Lett. 1991,1, 65.

    Article  CAS  Google Scholar 

  27. Chu, C. K., Babu, J. R., Beach, J. W. et al. J. Org. Chem. 1990, 55, 1418.

    Article  CAS  Google Scholar 

  28. Chu, C. K., Beach, J. W., Babu, J. R. et al. Nucleosides Nucleotides 1991,10, 423.

    Article  CAS  Google Scholar 

  29. Beach, J. W., Kim, H. O., Jeong, L. S. et al. J. Org. Chem. 1990,57, 3887.

    Article  Google Scholar 

  30. Bolon, P. J., Wang, P., Chu, C. K. et al. Bioorg. Med. Chem. Lett. 1996, 6, 1657.

    Article  CAS  Google Scholar 

  31. (a) Van Draanen, N. A., Koszalka, G. W. Nucleosides Nucleotides 1994, 13, 1679. (b) Van Draanen, N. A., Tisdale, M., Parry, N. R. et al. Antimicrob. Agents Chemother. 1994, 38, 868.

    Article  Google Scholar 

  32. (a) Burns, C L., St Clair, M. H., Frick, L. W. et al. J. Med. Chem. 1993, 36, 378. (b) Krenitsky, T. A., Koszalka, G. W., Tuttle, J. V. Biochemistry 1981, 20, 3615. (c) Elion, G. B. Carbohydrate Res. 1981, 97, 139.

    Article  CAS  Google Scholar 

  33. (a) Gosselin, G., Mathe, C., Bergogne, M.-C. et al. Nucleosides Nucleotides 1995, 14, 611. (b) Morvan, F., Génu, C, Rayner, B. et al. Biochem. Biophys. Res. Commun. 1990, 172, 537. (c) Génu-Dellac, C., Gosselin, G., Imbach, J.-L. Carbohydr. Res. 1991, 216, 249.

    Article  CAS  Google Scholar 

  34. (a) Gosselin, G., Bergogne, M.-C., Imbach, J.-L. J. Heterocyclic Chem. 1993, 30, 1229. (b) Génu-Dellac, C., Gosselin, G., Puech, F. et al. Nucleosides Nucleotides 1991, 10, 1345.

    Article  CAS  Google Scholar 

  35. Holy, A. Collect. Czech. Chem. Commun. 1972, 37, 4072.

    Article  CAS  Google Scholar 

  36. Lin, T.-S., Luo, M.-Z., Liu, M.-C. Tetrahedron Lett. 1994, 35, 3477.

    Article  CAS  Google Scholar 

  37. Lin, T.-S., Luo, M.-Z., Liu, M.-C. Tetrahedron, 1995, 51, 1055.

    Article  CAS  Google Scholar 

  38. Lin, T.-S., Luo, M.-Z., Liu, M.-C. et al. J. Med. Chem. 1996, 39, 1754.

    Article  Google Scholar 

  39. Génu-Dellac, C, Gosselin, G., Imbach, J.-L. Tetrahedron Lett. 1991, 32, 79.

    Article  Google Scholar 

  40. Gosselin, G., Schinazi, R. F., Sommadossi, J.-P. et al. Antimicrob. Agents Chemother. 1994, 38, 1292.

    Article  CAS  Google Scholar 

  41. Ma, T., Pai, B. S., Zhu, Y. L. et al. J. Med. Chem. 1996, 39, 2835.

    Article  CAS  Google Scholar 

  42. Chu, C. K., Shanmuganathan, K., Wang, C. G. et al. Antimicrob. Agents Chemother. 1995, 39, 979.

    Article  CAS  Google Scholar 

  43. Parker, R. B., Cheng, Y.-C. J. NIH Res. 1994, 6, 57.

    Google Scholar 

  44. McKenzie, R., Fried, M. W., Sallie, R. et al. Engl. J. Med. 1995, 333, 1099.

    Article  CAS  Google Scholar 

  45. Walker, T. E., Hagenkamp, H. P. C. Carbohydr. Res. 1974, 32, 413.

    Article  CAS  Google Scholar 

  46. Kenneth, J. R., Edward, M. A. in Synthetic Procedures in Nucleic Acids Chemistry, V. 1, Zorbach, W. W., Tipson, R. S. eds, Wiley, New York, 1968, pp. 163.

    Google Scholar 

  47. Abe, Y., Takizawa, C., Kunieda, T. Chem. Pharm. Bull. 1980, 28, 1324.

    Article  CAS  Google Scholar 

  48. Batch, A., Czernecki, S. J. Carbohydr. Chem. 1994, 13, 935.

    Article  CAS  Google Scholar 

  49. Chelain, E., Floch, O., Czernecki, S. J. Carbohydr. Chem. 1995,14, 1251.

    Article  CAS  Google Scholar 

  50. Oka, K., Wada, H. Yakugaku Zasshi. 1963, 83, 890; Chem Abstr. 1964, 60, 1825d.

    CAS  Google Scholar 

  51. Gosselin, G., Bergogne, M.-C., Imbach, J.-L. in Nucleic Acid Chemistry, Improved and New Synthetic Procedures, Methods and Techniques, Part 4, Townsend, L. B., Tipson, R. S. eds, Wiley, New York, 1991, pp. 41.

    Google Scholar 

  52. Robins, M. J., Samano, V., Johnson, M. D. J. Org. Chem. 1990, 55, 410.

    Article  CAS  Google Scholar 

  53. Xiang, Y. X., Calvacanti, S., Chu, C. K. et al. Bioorg. Med. Chem. Lett. 1995,5, 877.

    Article  CAS  Google Scholar 

  54. Xiang, Y., Kotra, L. P., Chu, C. K. Bioorg. Med. Chem. Lett. 1995, 5, 743.

    Article  CAS  Google Scholar 

  55. Hubschwerlen, C. Synthesis 1986, 962.

    Google Scholar 

  56. El Alaoui, A. M., Faraj, A., Pierra, C. et al. Antiviral. Chem. Chemother. 1996, 7, 276.

    Google Scholar 

  57. Schinazi, R. F., Chu, C. K., Kobra, B. E., Sommadossi, J.-P. Abstract 33rd ICAAC, New Orleans, 1993, 222427.

    Google Scholar 

  58. Chu, C. K., Beach, J. W., Jeong, L. S. et al. J. Org. Chem. 1991, 56, 6504.

    Google Scholar 

  59. Jeong, L. S., Alves, A. J., Carrigan, S. W. et al. Tetrahedron Lett. 1992, 32, 595.

    Article  Google Scholar 

  60. (a) Cammack, N. C., Rouse, P. L., Marr, C L. P. et al. Biochem. Pharmacol. 1992, 43, 2059. (b) Hart, G. J., Orr, D. C., Penn, C R. et al. Antimicrob. Agents Chemother. 1992, 36, 1688.

    Article  CAS  Google Scholar 

  61. Humber, D. C., Jones, M. F., Payne, J. J. et al. Tetrahedron Lett. 1992, 33, 4625.

    Article  CAS  Google Scholar 

  62. Andrews, G., Crawford, T. C., Bacon, B. E. J. Org. Chem. 1981, 46, 2976.

    Article  CAS  Google Scholar 

  63. (a) Lerner, L. M., Kohn, B. D., Kohn, P. J. Org. Chem. 1968, 33, 1780. (b) Evans, M. E., Parrish, F. W. Carbohydr. Res. 1973,28, 359.

    Article  CAS  Google Scholar 

  64. Chu, C. K., Beach, J. W., Jeong, L. S. et al. J. Org. Chem. 1991, 56, 6503.

    Article  CAS  Google Scholar 

  65. Whistler, R. L., Seib., P. A. Carbohydr. Res. 1966, 2, 93.

    Article  CAS  Google Scholar 

  66. Akagi, M., Tejima, S., Haga, M. Chem. Pharm. Bull. 1963,11, 58.

    Article  CAS  Google Scholar 

  67. Beach, J. W., Jeong, L. S., Kim, H. O. et al. in Nucleosides and Nucleotides as Antitumor and Antiviral Agents, Chu, C. K. and Baker, D. C. eds, Plenum Press, New York, 1993, pp. 219.

    Chapter  Google Scholar 

  68. Choi, W.-B., Wilson, L. J., Yeola, S. et al. J. Am. Chem. Soc. 1991,113, 9377.

    Article  CAS  Google Scholar 

  69. Romanelli, M., Teodori, E., Gualtieri, F. et al. J. Med. Chem. 1988, 31, 1698.

    Article  CAS  Google Scholar 

  70. Hope, D. B., Waltri, M. J. Chem. Soc. (C) 1970, 2475.

    Google Scholar 

  71. Nokami, J., Ryokume, K., Inada, J. Tetrahedron Lett. 1995, 36, 6099.

    Article  CAS  Google Scholar 

  72. Camplo, M., Charvet-Faury, A. S., Borel, C et al. Eur. J. Med. Chem. 1996, 31, 539.

    Article  CAS  Google Scholar 

  73. Kim, H. O., Schinazi, R. F., Shanmuganathan, K. et al. J. Med. Chem. 1993, 36, 519.

    Article  CAS  Google Scholar 

  74. Kim, H. O., Ann, S. K., Alves, A. J. et al. J. Med. Chem. 1992, 35, 1987.

    Article  CAS  Google Scholar 

  75. Chu, C. K., Ahn, S. K., Kim, H. O. et al. Tetrahedron Lett. 1991, 32, 3791.

    Article  CAS  Google Scholar 

  76. Kim, H. O., Shanmuganathan, K., Alves, A. J. et al. Tetrahedron Lett. 1992, 33, 6899.

    Article  CAS  Google Scholar 

  77. Grove, K. L., Cheng, Y. C Cancer Res. 1996, 56, 4187.

    CAS  Google Scholar 

  78. Stewart, L. C., Richtmeyer, N. K. J. Am. Chem. Soc. 1955, 77, 1021.

    Article  CAS  Google Scholar 

  79. Schinazi, R. F., Chen, M. S., Prusoff, W. H. J. Med. Chem. 1979, 22, 1273.

    Article  CAS  Google Scholar 

  80. Rahim, S. G., Trivedi, N., Bogunovic-Batchelor, M. V. et al. J. Med. Chem. 1996, 39, 789.

    Article  CAS  Google Scholar 

  81. Secrist, J. A., Tiwari, K. N., Riordan, J. M., Montgomery, J. A. J. Med. Chem. 1991, 34,2361.

    Article  CAS  Google Scholar 

  82. Secrist, J. A., Riggs, R. M., Tiwari, K. N., Montgomery, J. A. J. Med. Chem. 1992, 35, 533.

    Article  CAS  Google Scholar 

  83. Reist, E. J., Gueffroy, D. E., Goodman, L. J. Am. Chem. Soc. 1964,86, 5658.

    Article  CAS  Google Scholar 

  84. Wnuk, S. F. Tetrahedron 1993, 49, 9877 (review).

    Article  CAS  Google Scholar 

  85. Tiwari, K. N., Montgomery, J. A., Secrist J. A. Nucleosides Nucleotides 1993, 12, 841.

    Article  CAS  Google Scholar 

  86. Huang, B., Hui, Y. N. Nucleosides Nucleotides 1993, 12, 139.

    Article  CAS  Google Scholar 

  87. Dyson, M. R., Coe, P. L., Walker, R. T. Carbohydr. Res. 1991, 216, 237.

    Article  CAS  Google Scholar 

  88. Young, R. J., Shaw-Ponter, S., Thomson, J. B. et al. Bioorg. Med. Chem. Lett. 1995, 5, 2599.

    Article  CAS  Google Scholar 

  89. Shaw-Ponter, S., Rider, P., Young, R. J. Tetrahedron Lett. 1996, 37, 1871.

    Article  CAS  Google Scholar 

  90. Selwood, D. L., Carter, K., Young, R. J., Jandu, K. Bioorg. Med Chem. Lett. 1996, 6, 991.

    Article  CAS  Google Scholar 

  91. Uenishi, J., Takahashi, K., Motoyama, M. et al. Nucleosides Nucleotides 1994,13, 1347.

    Article  CAS  Google Scholar 

  92. (a) Shaw-Ponter, S., Rider, P., Young, R. J. Tetrahedron Lett. 1996, 37, 1867. (b) Tamaru, Y., Mitzutani, M., Furukawa, S. et al. J. Am. Chem. Soc. 1984,106, 1079.

    Article  CAS  Google Scholar 

  93. Nair, V., Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017.

    Article  CAS  Google Scholar 

  94. Bolon, P. J., Sells, T. B., Nuesca, Z. M. et al. Tetrahedron, 1994, 50, 7747.

    Article  CAS  Google Scholar 

  95. Nair, V., Emanuel, D. J. J. Am. Chem. Soc. 1977, 99, 1571.

    Article  CAS  Google Scholar 

  96. (a) Nair, V. Int. Antiviral News 1993, 1, 147. (b) Nair, V. U.S. Patent 5,231,174. (c) Nair, V., Nuesca, Z. M. J. Am. Chem. Soc. 1992,114, 7951. (d) Nair, V., Nuesca, Z. M., Purdy, D. F. et al. Antiviral Res. 1994, 23, 38. (e) Ohrui, H., Waga, T., Meguro, H. Biosci. Biotech. Biochem. 1993, 57, 1040.

    Google Scholar 

  97. (a) Kaspersen, F. M., Prandit, U. K. J. Chem. Soc. Perkin Trans. I 1975, 1798. (b) Kaspersen, F. M., Prandit, U. K. J. Chem. Soc. Perkin Trans. I 1975, 1617. (c) Peterson, M. L., Vince, R. J. Med. Chem. 1991, 34, 2787.

    Google Scholar 

  98. Sells, T. B., Nair, V. Tetrahedron Lett. 1992, 33, 7639.

    Article  CAS  Google Scholar 

  99. (a) Bamford, M. J., Humber, D. C., Storer, R. Tetrahedron Lett. 1991, 32, 271. (b) Sells, T. B., Nair, V. Tetrahedron 1994, 50, 117.

    Article  CAS  Google Scholar 

  100. (a) Montgomery, J. A., Thomas, H. J. J. Org. Chem. 1978, 43, 541. (b) Nair, V., Purdy, D. F. Heterocycle 1993, 36, 421. (c) Purdy, D. F., Zintek, L. B., Nair, V. Nucleosides Nucleotides 1994, 13, 109. (d) Zahler, R. V., Goodfellow, V. S., Ahmad, S. Eu Patent Appl. 0464769A2. (e) Zintek, L. B., Jeon, G. S., Nair, V. Heterocycle 1994, 37, 1853. (f) Tino, J. A., Clark, J. M., Field, A. K. et al. J. Med. Chem. 1993, 36, 1221.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer Science+Business Media New York

About this chapter

Cite this chapter

Agrofoglio, L.A., Challand, S.R. (1998). The chemistry of L-nucleosides. In: Acyclic, Carbocyclic and L-Nucleosides. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0816-7_6

Download citation

  • DOI: https://doi.org/10.1007/978-94-007-0816-7_6

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-3734-1

  • Online ISBN: 978-94-007-0816-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics