Glucose-derived 3'-(carboxymethyl)-3'-deoxyribonucleosides and 2',3'- lactones as synthetic precursors for amide-linked oligonucleotide analogues

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 2939-2945

  Robins, Morris J ^a   Doboszewsk, Bogdan ^a,b   Timoshchuk, Victor A ^a,c   Peterson, Matt A ^a  

^a Brigham Young University   (United States)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^c TriLink BioTechnologies Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYRIBONUCLEOTIDE; GLUCOSE DERIVATIVE; LACTONE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

DEOXYADENOSINES; GLUCOSE; INDICATORS AND REAGENTS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; OLIGONUCLEOTIDES; THYMIDINE;

EID: 0034686006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991399g     Document Type: Article

References (45)

1. Nucleic Acid Related Compounds. 111 (Amide-Linked Nucleosides. 3). For paper 110 (Amide-Linked Nucleosides. 2), see ref 8b.
2. (a) Garg, N.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1993, 49, 5189-5202.
3. (b) Ichikawa, S.; Shuto, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1997, 62, 1368-1375.
4. Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754, and references therein.
5. (a) Oligodeoxynucleotides. Antisense Inhibitors of Gene Expression; Cohen, J., Ed.; CRC Press: Boca Raton, 1989.
6. (b) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543-584.
7. Cazenave, C.; Hélène, C. In Antisense Nucleic Acids and Proteins; Mol, J. N. M., van der Krol, A. R., Eds.; Marcel Dekker: New York, 1991; pp 47-93.
8. Antisense Research and Applications; Crooke, S. T., Lebleu, B., Eds.; CRC Press: Boca Raton, 1993.
9. (a) Chu, C. K.; Doboszewski, B.; Schmidt, W.; Ullas, G. V.; Van Roey, P. J. Org. Chem. 1989, 54, 2767-2769.
10. (b) Sanghvi, Y. S.; Bharadwaj, R.; Debart, F.; De Mesmaeker, A. Synthesis 1994, 1163-1166.
11. (a) Fiandor, J.; Tam, S. Y. Tetrahedron Lett. 1990, 31, 597-600.
12. (b) Caulfield, T. J.; Prasad, C. V. C.; Prouty, C. P.; Saha, A. K.; Sardaro, M. P.; Schairer, W. C.; Yawman, A.; Upson, D. A.; Kruse, L. I. Bioorg. Med. Chem. Lett. 1993, 3, 2771-2776.
13. Grunder-Klotz, E.; Just, G. Nucleosides Nucleotides 1994, 13, 1829-1841.
14. Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199.
15. (e) Leitzel, J. C. Ph.D. Dissertation, The University of Chicago, 1996.
16. (f) Luo, P.; Leitzel, J. C.; Zhan, Z.-Y. J.; Lynn, D. G. J. Am. Chem. Soc. 1998, 120, 3019-3031.
17. (a) De Mesmaeker, A.; Lesueur, C.; Bévièrre, M.-O.; Waldner, A.; Fritsch, V.; Wolf, R. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2790-2794.
18. (b) von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876.
19. Lu, D.-M.; Min, J.-M.; Zhang, L.-H. Carbohydr. Res. 1999, 317, 193-197.
20. (a) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37, 3921-3924.
21. (b) Peterson, M. A.; Nilsson, B. L.; Sarker, S.; Doboszewski, B.; Zhang, W.; Robins, M. J. J. Org. Chem. 1999, 64, 8183-8192.
22. Xie, M.; Berges, D. A.; Robins, M. J. J. Org. Chem. 1996, 61, 5178-5179.
23. Yoshimura, Y.; Sano, T.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 162-167.
24. (a) Rosenthal, A.; Sprinzl, M. Can. J. Chem. 1968, 47, 4477-4481.
25. (b) Lourens, G. J.; Koekemoer, J. M. Tetrahedron Lett. 1975, 3715-3718.
26. Mazur, A.; Tropp, B. E.; Engel, R. Tetrahedron 1984, 40, 3949-3956.
27. Pudlo, J. S.; Townsend, L. B. Tetrahedron Lett. 1990, 31, 3101-3104.
28. (e) Hanessian, S. Total Synthesis of Natural Products: The "Chiron" Approach; Pergamon: New York, 1983.
29. (a) Mitsunobu, O. Synthesis 1981, 1-28.
30. (b) Hughes, D. L. Org. React. 1992, 42, 335-656.
31. Appel, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811.
32. Castro, B. R. Org. React. 1983, 29, 1-162.
33. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
34. Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York, 1994.
35. (a) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 3657-3660.
36. (b) Lourens, G. J.; Koekemoer, J. M. Tetrahedron Lett. 1975, 3719-3722.
37. Anderson R. C.; Fraser-Reid, B. J. Am. Chem. Soc. 1975, 97, 3870-3871.
38. Anderson, R. C.; Fraser-Reid, B. Tetrahedron Lett. 1977, 2865-2868.
39. Saneyoshi, M.; Satoh, E. Chem. Pharm. Bull. 1979, 27, 2518-2521.
40. Vorbrüggen, H. Acc. Chem. Res. 1995, 28, 509-520.
41. Kerwin, S. M.; Paul, A. G.; Heathcock, C. H. J. Org. Chem. 1987, 52, 1686-1695.
42. Fabrega, C.; Eritja, R.; Sinha, N. D.; Dosanjh, M. K.; Singer, B. Bioorg. Med. Chem. 1995, 3, 101-108.
43. (a) LaLonde, M.; Chan, T. H. Synthesis 1985, 817-845.
44. (b) Jones, D. M.; Nilsson, B.; Szelke, M.; J. Org. Chem. 1993, 58, 2286-2290.
45. Wolff, H. Org. React. 1947, III, 307-336.