Synthesis of a monophosphoryl lipid A derivative and its conjugation to a modified form of a tumor-associated carbohydrate antigen GM3

Chemical Communications

Volumn , Issue 37, 2009, Pages 5536-5537

  Wang, Qianli ^a   Xue, Jie ^a   Guo, Zhongwu ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE ANTIGEN; GANGLIOSIDE GM3; GLYCOCONJUGATE; PHOSPHORYL LIPID A;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONJUGATION; DRUG SYNTHESIS; IMMUNOSTIMULATION; PHOSPHOLIPID SYNTHESIS; QUANTUM MECHANICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 70349267664     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b907351e     Document Type: Article

References (24)

1. C. Erridge E. Bennett-Guerrero I. R. Poxton Microbes Infect. 2002 4 837
2. M. A. Dobrovolskaia S. N. Vogel Microbes Infect. 2002 4 903
3. D. H. Persing R. N. Coler M. J. Lacy D. A. Johnson J. R. Baldridge R. M. Hershberg S. G. Reed Trends Microbiol. 2002 10 10 s32
4. J. Baldridge, K. Myers, D. Johnson, D. Persing, C. Cluff and R. Hershberg, in Vaccine Adjuvants, ed., C. J. Hackett, and, D. A. J. Harn, Humana Press Inc., Totowa, NJ, 2006, pp. 235
5. J. R. Baldridge R. T. Crane Methods 1999 19 103
6. E. S. Van Amersfoort T. J. C. Van Berkel J. Kuiper Clin. Microbiol. Rev. 2003 16 379
7. N. Qureshi G. Kutuzova K. Takayama P. A. Rice D. T. Golenbock J. Endotoxin Res. 1999 5 147
8. D. C. Morrison R. Silverstein M. Luchi A. Shnyra Infect. Dis. Clin. N. Am. 1999 13 313
9. R. P. Darveau Curr. Opin. Microbiol. 1998 1 36
10. E. T. Rietschel T. Kirikae F. U. Schade U. Mamat G. Schmidt H. Loppnow A. J. Ulmer U. Zahringer S. U. F. Di Padova M. Schreier H. Brade FASEB J. 1994 8 217
11. E. Ribi J. Cantrell T. Feldner K. Myers J. Peterson Microbiology 1986 9
12. C. R. Casella T. C. Mitchell Cell. Mol. Life Sci. 2008 65 3231
13. S. J. Danishefsky J. R. Allen Angew. Chem., Int. Ed. 2000 39 836
14. H. J. Jennings and R. K. Sood, in Neoglycoconjugates: Preparation and Applications, ed., Y. C. Lee, and, R. T. Lee, Academic Press, San Diego, 1994, pp. 325
15. T. Buskas S. Ingale G.-J. Boons Angew. Chem., Int. Ed. 2005 44 5985
16. V. A. Kulshin U. Zähringer B. Lindner C. E. Frasch C. M. Tsai B. A. Dmitriev E. T. Rietschel J. Bacteriol. 1992 174 1793
17. T. Mochizuki Y. Iwano M. Shiozaki S. Kurakata S. Kanaic M. Nishijima Tetrahedron 2000 56 7691
18. H. Rembold R. R. Schmidt Carbohydr. Res. 1993 246 137
19. A. V. Demchenko M. A. Wolfert B. Santhanam J. N. Moore G.-J. Boons J. Am. Chem. Soc. 2003 125 6103
20. N. Yin R. L. Marshall S. Matheson P. B. Savage J. Am. Chem. Soc. 2003 125 2426
21. Z. Jiang W. A. Budzynski D. Qiu D. Yalamati R. R. Koganty Carbohydr. Res. 2007 342 784
22. Y. Zhang J. Gaekwad M. A. Wolfert G.-J. Boons J. Am. Chem. Soc. 2007 129 5200
23. Y. Fukase Y. Fujimoto Y. Adachi Y. Suda S. Kusumoto K. Fukase Bull. Chem. Soc. Jpn. 2008 81 796
24. Y. B. Pan P. Chefalo N. Nagy C. V. Harding Z. Guo J. Med. Chem. 2005 48 875