Deoxyribonucleoside cyclic N-acylphosphoramidites as a new class of monomers for the stereocontrolled synthesis of oligothymidylyl-and oligodeoxycytidylyl- phosphorothioates

Journal of the American Chemical Society

Volumn 122, Issue 10, 2000, Pages 2149-2156

  Wilk, Andrzej ^a   Grajkowski, Andrzej ^a   Phillips, Lawrence R ^b   Beaucage, Serge L ^a  

^a CENTER FOR BIOLOGICS EVALUATION AND RESEARCH   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYRIBONUCLEOSIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034653728     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991773u     Document Type: Article

References (61)

1. (a) Crooke, S. T.; Bennett, C. F. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 107-129.
2. (b) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194.
3. (a) Wilk, A.; Stec, W. J. Nucleic Acids Res. 1995, 23, 530-534.
4. (b) Wyrzykiewicz, T. K.; Cole, D. L. Bioorg. Chem. 1995, 23, 33-41.
5. Tang, J. Y.; Roskey, A.; Li, Y.; Agrawal, S. Nucleosides Nucleotides 1995, 14, 985-990.
6. Koziolkiewicz, M.; Wojcik, M.; Kobylanska, A.; Karwowski, B.; Rebowska, B.; Guga, P.; Stec, W. J. Antisense Nucleic Acid Drug Dev. 1997, 7, 43-48.
7. (a) Stec, W. J.; Grajkowski, A.; Koziolkiewicz, M.; Uznanski, B. Nucleic Acids Res. 1991, 19 5883-5888.
8. (b) Stec, W. J.; Grajkowski, A.; Kobylanska, A.; Karwowski, B.; Koziolkiewicz, M.; Misiura, K.; Okruszek, A.; Wilk, A.; Guga, P.; Boczkowska, M. J. Am. Chem. Soc. 1995, 117, 12019-12029.
9. (c) Karwowski, B.; Guga, P.; Kobylanska, A.; Stec, W. J. Nucleosides Nucleotides 1998, 17, 1747-1759.
10. (d) Stec, W. J.; Karwowski, B.; Boczkowska, M.; Guga, P.; Koziolkiewicz, M.; Sochacki, M.; Wieczorek, M. W.; Blaszczyk, J. J. Am. Chem. Soc. 1998, 120, 7156-7167.
11. (a) Wang, J.-C.; Just, G. Tetrahedron Lett. 1997, 38, 3797-3800.
12. (b) Wang, J.-C.; Just, G. Tetrahedron Lett. 1997, 38, 705-708.
13. (a) Jin, Y.; Just, G. J. Org. Chem. 1998, 63, 3647-3654.
14. (b) Jin, Y.; Biancotto, G.; Just, G. Tetrahedron Lett. 1996, 37, 973-976.
15. (a) Iyer, R. P.; Guo, M.-J.; Yu, D.; Agrawal, S. Tetrahedron Lett. 1998, 39, 2491-2494.
16. (b) Guo, M.-J.; Yu, D.; Iyer, R. P.; Agrawal, S. Bioorg. Med. Chem. Lett. 1998, 8, 2539-2544 and references therein.
17. This reaction was carried out essentially as described in the literature; see: (a) Mizrakh, L. I.; Polonskaya, L. Yu.; Kozlova, L. N.; Babushkina, T. A.; Bryantsev, B. I. Zh. Obshch. Khim. 1975, 45, 1469-1473. (b) Pudovik, M. A.; Terent'eva, S. A.; Medvedeva, M. D.; Pudovik, A. N. Zh. Obshch. Khim. 1973, 43, 679.
18. This reaction was carried out essentially as described in the literature; see: (a) Mizrakh, L. I.; Polonskaya, L. Yu.; Kozlova, L. N.; Babushkina, T. A.; Bryantsev, B. I. Zh. Obshch. Khim. 1975, 45, 1469-1473. (b) Pudovik, M. A.; Terent'eva, S. A.; Medvedeva, M. D.; Pudovik, A. N. Zh. Obshch. Khim. 1973, 43, 679.
19. 13C NMR signals associated with tertiary amide rotamers is well-documented in the literature; for example, see: (a) Abraham, R. J.; Loftus, P. In Proton and Carbon-13 NMR Spectroscopy -An Integrated Approach; Heyden: London, 1980; pp 171-174. (b) Edwards, O. E.; Dvornik, D.; Kolt, R. J.; Blackwell, B. A. Can. J. Chem. 1992, 70, 1397-1405. (c) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056- 2064. (d) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 1999, 64, 7515-7522.
20. 13C NMR signals associated with tertiary amide rotamers is well-documented in the literature; for example, see: (a) Abraham, R. J.; Loftus, P. In Proton and Carbon-13 NMR Spectroscopy - An Integrated Approach; Heyden: London, 1980; pp 171-174. (b) Edwards, O. E.; Dvornik, D.; Kolt, R. J.; Blackwell, B. A. Can. J. Chem. 1992, 70, 1397-1405. (c) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056- 2064. (d) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 1999, 64, 7515-7522.
21. 13C NMR signals associated with tertiary amide rotamers is well-documented in the literature; for example, see: (a) Abraham, R. J.; Loftus, P. In Proton and Carbon-13 NMR Spectroscopy - An Integrated Approach; Heyden: London, 1980; pp 171-174. (b) Edwards, O. E.; Dvornik, D.; Kolt, R. J.; Blackwell, B. A. Can. J. Chem. 1992, 70, 1397-1405. (c) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056-2064. (d) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 1999, 64, 7515-7522.
22. 13C NMR signals associated with tertiary amide rotamers is well-documented in the literature; for example, see: (a) Abraham, R. J.; Loftus, P. In Proton and Carbon-13 NMR Spectroscopy - An Integrated Approach; Heyden: London, 1980; pp 171-174. (b) Edwards, O. E.; Dvornik, D.; Kolt, R. J.; Blackwell, B. A. Can. J. Chem. 1992, 70, 1397-1405. (c) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056- 2064. (d) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Org. Chem. 1999, 64, 7515-7522.
23. 6.
24. 31P NMR spectrum (data shown in Experimental section and as Supporting Information).
25. Data shown as Supporting Information.
26. Hund, R.-D.; Behrens, U.; Röschenthaler, G.-V. Phosphorus, Sulfur, Silicon 1992, 69, 119-127.
27. Miller, G. R.; Yankowsky, A. W.; Grim, S. O. J. Chem. Phys. 1969, 51, 3185-3190.
28. (a) Everett, T. S. In Chemistry of Organic Fluorine Compounds II - A Critical Review, ACS Monograph 187; Hudlický, M., Pavlath, A. E., Eds.; American Chemical Society: Washington, DC, 1995; pp 1037-1086.
29. (b) Servis, K. L.; Fang, K.-N. J. Am. Chem. Soc. 1968, 90, 6712-6717.
30. (c) Chambers, R. D.; Sutcliffe, L. H.; Tiddy, G. J. T. Trans. Faraday Soc. 1970, 66, 1025-1038.
31. (d) Hilton, J.; Sutcliffe, L. H. Prog. Nucl. Magn. Reson. Spectros. 1975, 10, 27-39.
32. (e) Matthews, R. S.; Preston, W. E. Org. Magn. Reson. 1980, 14, 258-263.
33. (f) Matthews, R. S. Org. Magn. Reson. 1982, 18, 226-230.
34. Mallory, F. B.; Mallory, C. W.; Fedarko, M.-C. J. Am. Chem. Soc. 1974, 96, 3536-3542.
35. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Am. Chem. Soc. 1975, 97, 4770-4771.
36. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457-461.
37. p-1, out of potentially four diastereomers, can be isolated.
38. 3CN 2:1 v/v) = 0.71.
39. Numbering nomenclature of the oxygen, phosphorus, and nitrogen atoms of the oxazaphospholane ring is 1, 2, and 3, respectively. See: Phosphor-Verbindungen II, Houben-Weyl - Methoden der organischen Chemie, Band E2; Georg Thieme Verlag Stuttgart: New York, 1982; pp 1125-1126.
40. Complete elution of deoxyribonucleoside cyclic N-acylphosphoramidites from silica gel columns should be accomplished within 2 h to minimize decomposition.
41. p-9.
42. (a) Beaucage, S. L.; Iyer, R. P.; Egan, W.; Regan, J. B. Ann. New York Acad. Sci. 1990, 616, 483-485.
43. (b) Iyer, R. P.; Phillips, L. R.; Egan, W.; Regan, J. B.; Beaucage, S. L. J. Org. Chem. 1990, 55, 4693-4699.
44. (c) Regan, J. B.; Phillips, L. R.; Beaucage, S. L. Org. Prep. Proced. Int. 1992, 24, 488-492.
45. 31P NMR spectroscopy.
46. Mizrakh, L. I.; Polonskaya, L. Yu.; Babushkina, T. A.; Bryantsev, B. I. Zh. Obshch. Khim. 1975, 45, 549-552.
47. 2O (1:1 v/v) for further experimentation.
48. Brown, D. M.; Osborne, G. O. J. Chem. Soc. 1957, 2590-2593.
49. (a) Wilk, A.; Srinivasachar, K.; Beaucage, S. L. J. Org. Chem. 1997, 62, 6712-6713.
50. (b) Wilk, A.; Grajkowski, A.; Srinivasachar, K.; Beaucage, S. L. Antisense Nucleic Acid Drug Dev. 1999, 9, 361-366.
51. (a) van Boom, J. H.; Burgers, P. M. J.; van Deursen, P. H.; Arentzen, R.; Reese, C. B. Tetrahedron Lett. 1974, 3785-3788.
52. (b) Adamiak, R. W.; Arentzen, R.; Reese, C. B. Tetrahedron Lett. 1977, 1431-1434.
53. (c) Reese, C. B.; Titmas, R. C.; Yau, L. Tetrahedron Lett. 1978, 2727-2730.
54. (a) Daub, G. W.; van Tamelen, E. E. J. Am. Chem. Soc. 1977, 99, 3526-3528.
55. (b) Brill, W. K.-D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 3972-3980.
56. (c) Caruthers, M. H.; Kierzek, R.; Tang, J. Y. In Biophosphates and Their Analogues - Synthesis, Structure, Metabolism and Activity: Bruzik, K. S., Stec, W. J., Eds; Elsevier: Amsterdam, 1987; pp 3-21.
57. Ho, T.-L. Chem. Rev. 1975, 75, 1-20.
58. Wilk, A.; Uznanski, B.; Stec, W. J. Nucleic Acids Res. Symp. Ser. No. 24 1991, 63-66.
59. p-9.
60. This CPG support was prepared as reported in the literature; see: Brown, T.; Pritchard, C. E.; Turner, G.; Salisbury, S. A. J. Chem. Soc., Chem. Commun. 1989, 891-893.
61. Boal, J. H.; Wilk, A.; Harindranath, N.; Max, E. E.; Kempe, T.; Beaucage, S. L. Nucleic Acids Res. 1996, 24, 3115-3117.