Synthesis of QS-21-based immunoadjuvants

Journal of Organic Chemistry

Volumn 78, Issue 22, 2013, Pages 11525-11534

  Wang, Pengfei ^a   Dai, Qipu ^a   Thogaripally, Punith ^a   Zhang, Ping ^a   Michalek, Suzanne M ^b  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b University of Alabama at Birmingham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL GLYCOSIDES; BUILDING BLOCKES; EFFICIENT SYNTHESIS; IMMUNOADJUVANTS;

CHEMISTRY;

ORGANIC COMPOUNDS;

2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL(1-3) 2,4 DI O ACETYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 DI O ACETYL ALPHA LEVO RHAMNOPYRANOSYL( 1-2) 3,4 DI O ACETYL ALPHA DEXTRO FUCOPYRANOSYL TRICHLOROACETIMIDATE; 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 DI O ACETYL ALPHA LEVO RHAMNOPYRANOSYL(1-2) 3,4 DI O ACETYL ALPHA DEXTRO FUCOPYRANOSYL TRICHLOROACETIMIDATE; 2,3,5 TRI O ACETYL BETA DEXTRO APIOFURANOSYL (1-3) 2,4 DI O ACETYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 O DIACETYL ALPHA LEVO RHAMNOPYRANOSYL(1-2) 3,4 DI O ACETYL ALPHA DEXTRO FUCOPYRANOSYL TRICHLOROACETIMIDATE; ALLYL 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL(1-2) 3,4 O ISOPROPYLIDENE ALPHA DEXTRO FUCOPYRANOSIDE; ALLYL 2,3,4 TRI O PIVALOYL ALPHA DEXTRO XYLOPYRANOSIDE; ALLYL 2,3,4 TRI O PIVALOYL BETA DEXTRO XYLOPYRANOSYL(1-3) 2,4 DI O PIVALOYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL( 1-2) 3,4 O ISOPROPYLIDENE ALPHA DEXTRO FUCOPYRANOSIDE; ALLYL 2,3,4 TRI O PIVALOYL BETA DEXTRO XYLOPYRANOSYL(1-3) 2,4 DI OPIVALOYL ALPHA DEXTRP XYLOPYRANOSIDE; ALLYL 2,3,4 TRI O PIVALOYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL(1-2) 3,4 O ISOPROPYLIDENE ALPHA DEXTRO FUCOPYRANOSIDE; ALLYL 2,3,5 TRI O ACETYL BETA DEXTRO APIOFURANOSYL(1-3) 2,4 DI O PIVALOYL BETA DEXTRO XYLOPYRANOSYL(1-4) 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSYL( 1-2) 3,4 O ISOPROPYLIDENE ALPHA DEXTRO FUCOPYRANOSIDE; ALLYL 2,3,5 TRI O ACETYL BETA DEXTRO APIOFURANOSYL(1-3) 2,4 DI OPIVALOYL BETA DEXTRO XYLOPYRANOSIDE; ALLYL 2,4 DI O PIVALOYL ALPHA DEXTRO XYLOPYRANOSIDE; ALLYL 3,4 ISOPROPYLIDENE ALPHA DEXTRO FUCOPYRANOSIDE; ALLYL 4 O ACETYL 2,3 O ISOPROPYLIDENE ALPHA LEVO RHAMNOPYRANOSIDE; GLYCOSIDE; IMMUNOLOGICAL ADJUVANT; QS 21; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; GLYCOSYLATION; MOUSE; NONHUMAN;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; CARBOHYDRATE CONFORMATION; FEMALE; HEMAGGLUTININS; MICE; MICE, INBRED BALB C; MOLECULAR SEQUENCE DATA; SAPONINS;

EID: 84887944027     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402118j     Document Type: Article

References (39)

1. Ragupathi, G.; Gardner, J. R.; Livingston, P. O.; Gin, D. Y. Expert Rev. Vaccines 2011, 10, 463
2. Brunner, R.; Jensen-Jarolim, E.; Pali-Scholl, I. Immunol. Lett. 2010, 128, 29
3. Kensil, C. R.; Mo, A. X.; Truneh, A. Front. Biosci. 2004, 9, 2972
4. Leroux-Roels, G. Vaccine 2010, 28 (Suppl. 3) C25
5. Kensil, C. R.; Liu, G.; Anderson, C.; Storey, J. In Vaccine Adjuvants: Immunological and Clinical Principles; Hackett, C. J.; Harn, D. A. J., Eds.; Humana Press Inc.: Totowa, NJ, 2005; p 221.
6. Kensil, C. R.; Patel, U.; Lennick, M.; Marciani, D. J. Immunol. 1991, 146, 431
7. Deng, K.; Adams, M. M.; Damani, P.; Livingston, P. O.; Ragupathi, G.; Gin, D. Y. Angew. Chem., Int. Ed. 2008, 47, 6395
8. Wang, P.; Kim, Y.-J.; Navarro-Villalobos, M.; Rohde, B. D.; Gin, D. Y. J. Am. Chem. Soc. 2005, 127, 3256
9. Ragupathi, G.; Damani, P.; Deng, K.; Adams, M. M.; Hang, J.; George, C.; Livingston, P. O.; Gin, D. Y. Vaccine 2010, 28, 4260
10. Kensil, C. R. Crit. Rev. Ther. Drug Carrier Syst. 1996, 13, 1
11. Marciani, D.; Press, J. B.; Reynolds, R. C.; Pathak, A. K.; Pathak, V.; Gundy, L. E.; Farmer, J. T.; Koratich, M. S.; May, R. D. Vaccine 2000, 18, 3141
12. Marciani, D. J.; Pathak, A. K.; Reynolds, R. C.; Seitz, L.; May, R. D. Int. Immunopharmacol. 2001, 1, 813
13. Marciani, D. J.; Ptak, R. G.; Voss, T. G.; Reynolds, R. C.; Pathak, A. K.; Chamblin, T. L.; Scholl, D. R.; May, R. D. Int. Immunopharmacol. 2002, 2, 1703
14. Marciani, D. J.; Reynolds, R. C.; Pathak, A. K.; Finley-Woodman, K.; May, R. D. Vaccine 2003, 21, 3961
15. Adams, M. M.; Damani, P.; Perl, N. R.; Won, A.; Hong, F.; Livingston, P. O.; Ragupathi, G.; Gin, D. Y. J. Am. Chem. Soc. 2010, 132, 1939
16. Chea, E. K.; Fernandez-Tejada, A.; Damani, P.; Adams, M. M.; Gardner, J. R.; Livingston, P. O.; Ragupathi, G.; Gin, D. Y. J. Am. Chem. Soc. 2012, 134, 13448
17. Soltysik, S.; Wu, J.-Y.; Recchia, J.; Wheeler, D. A.; Newman, M. J.; Coughlin, R. T.; Kensil, C. R. Vaccine 1995, 13, 1403
18. Liu, G.; Anderson, C.; Scaltreto, H.; Barbon, J.; Kensil, C. R. Vaccine 2002, 20, 2808
19. Marciani, D. J.; Pathak, A. K.; Reynolds, R. C. Vaccine 2002, 20, 3237
20. Higuchi, R.; Tokimitsu, Y.; Fujioka, T.; Komori, T.; Kawasaki, T.; Oakenful, D. G. Phytochemistry 1987, 26, 229
21. Wang, P.; Haldar, P.; Wang, Y.; Hu, H. J. Org. Chem. 2007, 72, 5870
22. Wang, Y.; Liang, X.; Wang, P. Tetrahedron Lett. 2011, 52, 3912
23. Wang, Y.; Zhang, X.; Wang, P. Org. Biomol. Chem. 2010, 8, 4322
24. Yang, H.; Wang, P. J. Org. Chem. 2013, 78, 1858
25. Mahajan, R.; Dixit, S.; Khare, N. K.; Khare, A. J. Carbohydr. Chem. 1994, 13, 63
26. Liu, M.; Yu, B.; Wu, X.; Hui, Y.; Fung, K.-P. Carbohydr. Res. 2000, 329, 745
27. Baudry, D.; Ephritikhine, M.; Felkin, H. J. Chem. Commun. 1978, 694
28. Oltyoort, J. J.; Boeckel, V.; A., C. A.; De Koning, J. H.; Van Boom, J. H. Synthesis 1981, 305
29. Harreus, A.; Kunz, H. Liebigs Ann. Chem. 1986, 717
30. Kunz, H.; Sager, W. Helv. Chim. Acta 1985, 68, 283
31. Carpino, L. J. Am. Chem. Soc. 1993, 115, 4397
32. Pillion, D. J.; Amsden, J. A.; Kensil, C. R.; Recchia, J. J. Pharm. Sci. 1996, 85, 518
33. Gaddis, D. E.; Maynard, C. L.; Weaver, C. T.; Michalek, S. M.; Katz, J. J. Leukocyte Biol. 2013, 93, 21
34. Gaddis, D. E.; Michalek, S. M.; Katz, J. Mol. Immunol. 2009, 46, 2493
35. Gaddis, D. E.; Michalek, S. M.; Katz, J. J. Immunol. 2011, 186, 5772
36. Yang, Q.-B.; Martin, M.; Michalek, S. M.; Katz, J. Infect. Immun. 2002, 70, 3557
37. Zhang, P.; Martin, M.; Michalek, S. M.; Katz, J. Infect. Immun. 2005, 73, 3990
38. Zhang, P.; Martin, M.; Yang, Q.-B.; Michalek, S. M.; Katz, J. Infect. Immun. 2004, 72, 637
39. Zhang, P.; Yang, Q.-B.; Marciani, D. J.; Martin, M.; Clements, J. D.; Michalek, S. M.; Katz, J. Vaccine 2003, 21, 4459