Cyclic phosphate-linked oligosaccharides: Synthesis and conformational behavior of novel cyclic oligosaccharide analogues

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3395-3408

  Di Fabio, Giovanni ^a   Randazzo, Antonio ^a   D'Onofrio, Jennifer ^a   Ausín, Cristina ^b,c   Pedroso, Enrique ^b   Grandas, Anna ^b   De Napoli, Lorenzo ^a   Montesarchio, Daniela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF BARCELONA   (Spain)

^c CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC DIMER; CYCLIC PHOSPHATE-LINKED OLIGOSACCHARIDES; LINEAR PRECURSORS; PHOSPHODIESTER BONDS;

CHEMICAL BONDS; CONFORMATIONS; DIMERS; DNA; GLUCOSE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

POLYSACCHARIDES;

CYCLIC PHOSPHATE LINKED OLIGOSACCHARIDE; DIMER; GLUCOPYRANOSIDE; GLUCOSE; OLIGOSACCHARIDE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; DNA SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CYTOCHROME P-450 ENZYME SYSTEM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OLIGOSACCHARIDES; PHOSPHATES; PLANT PROTEINS;

EID: 33646266527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0600757     Document Type: Article

References (45)

1. For recent reviews on macrocycles, see: (a) Roxburgh, C. J. Tetrahedron 1995, 51, 9767-9822.
2. (b) Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 10, 1949-1964.
3. (c) Gonthier, E.; Breinbauer, R. Mol. Diversity 2005, 9, 51-62.
4. (d) Wessjohann, L. A.; Ruijter, E. Top. Curr. Chem. 2005, 243, 137-184.
5. For a comprehensive review on cyclodextrins, see: Szejtli, J. Chem. Rev. 1998, 98, 1743-1753 and references therein.
6. (a) Davis, M. E.; Brewster, M. E. Nat. Rev. Drug Discovery 2004, 3, 1023-1035.
7. (b) Nalluri, B. N.; Chowdary, K. P. R.; Murthy, K. V. R. Int. J. Pharm. Excipients 2002, 79-91.
8. Takahashi, K. Chem. Rev. 1998, 98, 2013-2034.
9. Rajewski, R. A.; Stella, V. J. J. Pharm. Sci. 1996, 85, 1142-1169.
10. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.
11. Willner, I.; Willner, B. J. Mater. Chem. 1998, 8, 2543-2556.
12. Mitchell, C. R.; Armstrong, D. W. Methods Mol. Biol. 2004, 243, 61-112.
13. Hedged, A. Chem. Rev. 1998, 98, 2035-2044.
14. Easton, C. J.; Lincoln, S. F. Modified Cyclodextrins: Scaffolds and Templates for Supramolecular Chemistry; Imperial College Press: London, 1999.
15. (a) Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977-1996.
16. (b) Engeldinger, E.; Armspach, D.; Matt, D. Chem. Rev. 2003, 105, 4147-4173.
17. (a) Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919-1958.
18. (b) Yuan, D. Q.; Tahara, T.; Chen, W. H.; Okabe, Y.; Yang, C.; Yagi, Y.; Nogami, Y.; Fukudome, M.; Fujita, K. J. Org. Chem. 2003, 68, 9456-9466.
19. (c) Kida, T.; Kikuzawa, A.; Nakatsuji, Y.; Akashi, M. Chem. Commun. 2003, 3020-3021.
20. (a) Fan, L.; Hindsgaul, O. Org. Lett. 2002, 4, 4503-4506.
21. (b) Locardi, E.; Stockle, M.; Gruner, S.; Kessler, H. J. Am. Chem. Soc. 2001, 123, 8189-8196.
22. (c) van Well, R. M.; Marinelli, L.; Erkelens, K.; van der Marel, G. A.; Lavecchia, A.; Overkleeft, H. S.; van Boom, J. H.; Kessler, H.; Overhand, M. Eur. J. Org. Chem. 2003, 2303-2313.
23. (d) Bornaghi, L. F.; Wilkinson, B. L.; Kiefel, M. J.; Poulsen, S. A. Tetrahedron Lett. 2004, 45, 9281-9284.
24. (e) von Roedern, E. G.; Lohof, E.; Hessler, G.; Hoffmann, M.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 10156-10167.
25. (f) van Well, R. M.; Overkleeft, H. S.; Overhand, M.; Carstenen, E. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 9331-9335.
26. (g) van Well, R. M.; Marinelli, L.; Altona, C.; Erkelens, K.; Siegal, G.; van Raaij, M.; Llamas-Saiz, A. L.; Kessler, H.; Novellino, E.; Lavecchia, A.; van Boom, J. H.; Overhand, M. J. Am. Chem. Soc. 2003, 125, 10822-10829.
27. (h) Mayes, B. A.; Stetz, R. J. E.; Ansell, C. W. G.; Fleet, G. W. J. Tetrahedron Lett. 2004, 45, 153-156.
28. (i) Stichler-Bonaparte, J.; Vasella, A. Helv. Chim. Acta 2001, 84, 2355-2367.
29. (j) Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265-287.
30. (k) Bürli, R.; Vasella, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1852-1853.
31. (l) Morales, J. C.; Zurita, D.; Penadés, S. J. Org. Chem. 1998, 63, 9212-9222.
32. (m) Belghiti, T.; Joly, J.-P.; Alem, H.; Chapleur, Y. C. R. Chim. 2003, 6, 553-564.
33. (n) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638-1639.
34. (o) Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 4479-4482.
35. (p) Velasco-Torrijos, T.; Murphy, P. V. Tetrahedron: Asymmetry 2005, 76, 261-272.
36. Nicolaou, K. C.; Florke, H.; Egan, H.; Egan, M. G.; Barth, T.; Estevez, V. A. Tetrahedron Lett. 1995, 36, 1775-1778.
37. Alazzouzi, E. M.; Escaja, N.; Grandas, A.; Pedroso, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1506-1508.
38. Rivaille, R.; Szabó, L. Bull. Soc. Chim. Fr. 1963, 716-721.
39. Ziegler, T.; Eckhardt, E.; Herold, G. Liebigs Ann. Chem. 1992, 5, 441-451.
40. Adinolfi, M.; De Napoli, L.; Di Fabio, G.; Iadonisi, A.; Montesarchio, D.; Piccialli, G. Tetrahedron 2002, 58, 6697-6704.
41. De Napoli, L.; Galeone, A.; Mayol, L.; Messere, A.; Montesarchio, D.; Piccialli, G. Bioorg. Med. Chem. 1995, 3, 1325-1329 and references therein.
42. (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 2000, 83, 995-1021.
43. (b) Bernet, B.; Vasella, A. Helv. Chim. Acta 2000, 83, 2055-2071.
44. (c) Ivarsson, I.; Sandström, C.; Sandström, A.; Kenne, L. J. Chem. Soc., Perkin Trans. 2 2000, 2, 2147-2152.
45. Lankhorst, P. P.; Haasnoot, C. A. G.; Erkelens, C.; Altona, C. J. Biomol. Struct. Dyn. 1984, 1, 1387-1405.