Synthesis of fungal glycolipid asperamide B and investigation of its ability to stimulate natural killer T cells

Organic Letters

Volumn 15, Issue 20, 2013, Pages 5242-5245

  Chaudhary, Vinod ^a   Albacker, Lee A ^b   Deng, Shenglou ^a   Chuang, Ya Ting ^b   Li, Yubo ^a   Umetsu, Dale T ^b   Savage, Paul B ^a  

^a Brigham Young University   (United States)

^b BOSTON CHILDREN S HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-O-BETA-D-GLUCOPYRANOSYL-(2S,2'R,3R,3'E,4E,8E)-N-(2'-HYDROXY-3'-HEXADECENOYL)-9-METHYL-4,8-ICOSADIEN-1,3-DIOL; 1 O BETA D GLUCOPYRANOSYL (2S,2'R,3R,3'E,4E,8E) N (2' HYDROXY 3' HEXADECENOYL) 9 METHYL 4,8 ICOSADIEN 1,3 DIOL; GAMMA INTERFERON; INTERLEUKIN 4; SPHINGOLIPID;

ANIMAL; ARTICLE; ASPERGILLUS; CHEMISTRY; CONFORMATION; DENDRITIC CELL; DOSE RESPONSE; DRUG EFFECT; ENZYME LINKED IMMUNOSORBENT ASSAY; MOUSE; NATURAL KILLER T CELL; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ASPERGILLUS; DENDRITIC CELLS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME-LINKED IMMUNOSORBENT ASSAY; INTERFERON-GAMMA; INTERLEUKIN-4; MICE; MOLECULAR CONFORMATION; NATURAL KILLER T-CELLS; SPHINGOLIPIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886256905     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4024375     Document Type: Article

References (20)

1. Agarwal, R. Curr. Allergy Asthma Rep. 2011, 11, 403-413
2. Menzies, D.; Holmes, L.; McCumesky, G.; Prys-Picard, C.; Niven, R. Allergy 2011, 66, 679-685
3. Kim, H. Y.; DeKruyff, R. H.; Umetsu, D. T. Nat. Immunol. 2010, 11, 577-584
4. Albacker, L. A.; Chaudhary, V.; Chang, Y.-J.; Kim, H. Y.; Chuang, Y.-T.; Pichavant, M.; DeKruyff, R. H.; Savage, P. B.; Umetsu, D. T. Nat. Med. 2013, 19, 1297-1304
5. Bendelac, A.; Savage, P. B.; Teyton, L. Annu. Rev. Immunol. 2007, 25, 297-336
6. Matangkasombut, P.; Pichavant, M.; Dekruyff, R. H.; Umetsu, D. T. Mucosal Immunol. 2009, 2, 383-392
7. Scanlon, S.; Thomas, S.; Ferreira, C. M.; Bai, L.; Krausz, T.; Savage, P. B.; Bendelac, A. J. Exp. Med. 2011, 208, 2113-2124
8. Balloy, V.; Chignard, M. Microbes Infect. 2009, 11, 919-927
9. Toledo, M. S.; Levery, S. B.; Straus, A. H.; Suzuki, E.; Momany, M.; Glushka, J.; Moulton, J. M.; Takahashi, H. K. Biochemistry 1999, 38, 7294-7306
10. Zhang, Y.; Wang, S.; Li, X.-M.; Cui, C.-M.; Feng, C.; Wang, B.-G. Lipids 2007, 42, 759-764
11. Kawai, G.; Ikeda, Y.; Tubaki, K. Agric. Biol. Chem. 1985, 49, 2137-2146
12. Mori, K.; Uenishi, K. Liebigs Ann. 1996, 1-6
13. Savage, P. B.; Bendelac, A.; Teyton, L. Chem. Soc. Rev. 2006, 35, 771-779
14. Pellicci, D. G.; Clark, A. J.; Patel, O.; Mallevaey, T.; Beddoe, T.; Le Nours, J.; Ulrich, A. P.; McClusky, J.; Besra, G. S.; Porcelli, S. A.; Gapin, L.; Godfrey, D. I.; Rossjohn, J. Nat. Immunol. 2011, 12, 827-833
15. Folch, J.; Lees, M.; Sload-Stanley, G. H. J. Biol. Chem. 1957, 226, 497-509
16. Kim, H. Y.; Salem, N., Jr. J. Lipid Res. 1990, 31, 2285-2289
17. Murakami, T.; Hirono, R.; Furusawa, K. Tetrahedron 2005, 61, 9233-9241
18. Negishi, E. Acc. Chem. Res. 1987, 20, 65-72
19. Prévost, S.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V. Adv. Synth. Catal. 2011, 353, 3213-3226
20. Liu, Y.; Goff, R. D.; Zhou, D.; Mattner, J.; Sullivan, B. A.; Khurana, A.; Cantu, C.; Altman, J. D.; Teyton, L.; Bendelac, A.; Savage, P. B. J. Immunol. Methods 2006, 312, 34-39