Total synthesis of an immunomodulatory phosphoglycolipid from thermophilic bacteria

Chemistry - A European Journal

Volumn 19, Issue 24, 2013, Pages 7989-7998

  Lin, Hong Jyune ^a   Adak, Avijit Kumar ^a   Reddy, L Vijaya Raghava ^a   Wu, Shih Hsiung ^b   Lin, Chun Cheng ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

diastereoselectivity; glycolipids; glycosylation; immunomodulators; phosphoglycolipids; total synthesis

Indexed keywords

DIASTEREO-SELECTIVITY; GLYCOLIPIDS; IMMUNOMODULATORS; PHOSPHOGLYCOLIPIDS; TOTAL SYNTHESIS;

BACTERIA; ESTERIFICATION; GLYCOSYLATION; PHOSPHOLIPIDS;

SYNTHESIS (CHEMICAL);

ACETAMIDE DERIVATIVE; CHLOROACETIC ACID; IMMUNOLOGICAL ADJUVANT; LYXOSE; PENTOSE; PHOSPHOLIPID; SILANE DERIVATIVE; TRICHLOROACETAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; SYNTHESIS; THERMUS;

ACETAMIDES; ADJUVANTS, IMMUNOLOGIC; CHLOROACETATES; GLYCOSYLATION; MOLECULAR STRUCTURE; PENTOSES; PHOSPHOLIPIDS; SILANES; THERMUS;

EID: 84878533232     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204550     Document Type: Article

References (49)

1. B. Beutler, E. T. Rietschel, Nat. Rev. Immunol. 2003, 3, 169-176
2. A. Aderem, R. J. Ulevitch, Nature 2000, 406, 782-787.
3. S. Leone, A. Molinaro, B. Lindner, I. Romano, B. Nicolaus, M. Parrilli, R. Lanzetta, O. Holst, Glycobiology 2006, 16, 766-775
4. F.-L. Yang, C.-P. Lu, C.-S. Chen, H.-L. Hsiao, Y. Su, S.-S. Tsay, W. Zou, S.-H. Wu, Eur. J. Biochem. 2004, 271, 4545-4551
5. A. Silipo, A. Molinaro, C. de Castro, R. Ferrara, I. Romano, B. Nicolaus, R. Lanzetta, M. Parrilli, Eur. J. Org. Chem. 2004, 2004, 5047-5054
6. T.-L. Lu, C.-S. Chen, F.-L. Yang, J.-M. Fung, M.-Y. Chen, S.-S. Tsay, J. Li, W. Zou, S.-H. Wu, Carbohydr. Res. 2004, 339, 2593-2598
7. A. M. Ferreira, R. Wait, M. F. Nobre, M. S. da Costa, Microbiology 1999, 145, 1191-1199
8. R. A. Pask-Hughes, N. J. Shaw, J. Bacteriol. 1982, 149, 54-58.
9. S. I. Miller, R. K. Ernst, M. W. Bader, Nat. Rev. Microbiol. 2005, 3, 36-46
10. Y. Kinjo, D. Wu, G. Kim, G. W. Xing, M. A. Poles, D. D. Ho, K. Kawahara, C.-H. Wong, M. Kronenberg, Nature 2005, 434, 520-525
11. Y. Kinjo, E. Tupin, D. Wu, M. Fujio, R. Garcia-Navarro, M. R. E. I. Benhnia, D. M. Zajonc, G. Ben-Menachem, G. D. Ainge, G. F. Painter, A. Khurana, K. Hoebe, S. M. Behar, B. Beutler, I. A. Wilson, M. Tsuji, T. J. Sellati, C.-H. Wong, M. Kronenberg, Nat. Immunol. 2006, 7, 978-986
12. D. B. Stetson, M. Mohrs, R. L. Reinhardt, J. L. Baron, Z. E. Wang, L. Gapin, M. Kronenberg, R. M. Locksley, J. Exp. Med. 2003, 198, 1069-1076.
13. Y.-L. Yang, F.-L. Yang, S.-C. Jao, M.-Y. Chen, S.-S. Tsay, W. Zou, S.-H. Wu, J. Lipid Res. 2006, 47, 1823-1832
14. Y. Suda, F. Okazaki, Y. Hasegawa, S. Adachi, K. Fukase, S. Kokubo, S. Kuramitsu, S. Kusumoto, PLoS ONE 2012, 7, e 35067.
15. Y.-L. Yang, K.-F. Hua, F.-L. Yang, Z. Wei, Y.-P. Chen, S.-M. Liang, H.-Y. Hsu, S.-H. Wu, Glycoconjugate J. 2008, 25, 427-439.
16. G.-T. Fan, Y.-S. Pan, K.-C. Lu, Y.-P. Cheng, W.-C. Lin, S. Lin, C.-H. Lin, C.-H. Wong, J.-M. Fang, C.-C. Lin, Tetrahedron 2005, 61, 1855-1862.
17. L.-C. Hung, C.-C. Lin, S.-K. Hung, B.-C. Wu, M.-D. Jan, S.-H. Liou, S.-L. Fu, Biochem. Pharmacol. 2007, 73, 1957-1970
18. L.-D. Huang, H.-J. Lin, P.-H. Huang, W.-C. Hsiao, L. V. R. Reddy, S.-L. Fu, C.-C. Lin, Org. Biomol. Chem. 2011, 9, 2492-2504.
19. Y.-S. Lin, L.-D. Huang, C.-H. Lin, P.-H. Huang, Y.-J. Chen, F.-H. Wong, C.-C. Lin, S.-L. Fu, J. Biol. Chem. 2011, 286, 43782-43792.
20. Y. Huang, R. Anderson, J. Biol. Chem. 1989, 264, 18667-18672.
21. X. Zhu, R. R. Schmidt, Angew. Chem. 2009, 121, 1932-1967
22. Angew. Chem. Int. Ed. 2009, 48, 1900-1934
23. J. D. C. Codée, R. Litjens, L. J. van den Bos, H. S. Overkleeft, G. A. van der Marel, Chem. Soc. Rev. 2005, 34, 769-782.
24. C.-C. Lin, G.-T. Fan, J.-M. Fang, Tetrahedron Lett. 2003, 44, 5281-5283
25. C.-W. Chang, Y.-N. Chen, A. K. Adak, K.-H. Lin, D.-L. M. Tzou, C.-C. Lin, Tetrahedron 2007, 63, 4310-4318.
26. A. F. G. Bongat, A. V. Demchenko, Carbohydr. Res. 2007, 342, 374-406
27. R. E. J. N. Litjens, L. J. van den Bos, J. D. C. Codee, H. S. Overkleeft, G. A. van der Marel, Carbohydr. Res. 2007, 342, 419-429.
28. K. Benakli, C. Zha, R. J. Kerns, J. Am. Chem. Soc. 2001, 123, 9461-9462.
29. D. Crich, A. U. Vinod, Org. Lett. 2003, 5, 1297-1300.
30. S. Manabe, K. Ishii, Y. Ito, J. Am. Chem. Soc. 2006, 128, 10666-10667.
31. T. G. Mayer, B. Kratzer, R. R. Schmidt, Angew. Chem. 1994, 106, 2289-2293
32. Angew. Chem. Int. Ed. Engl. 1994, 33, 2177-2181.
33. J. Park, S. Kawatkar, J.-H. Kim, G.-J. Boons, Org. Lett. 2007, 9, 1959-1962.
34. Y. Geng, L.-H. Zhang, X.-S. Ye, Tetrahedron 2008, 64, 4949-4958.
35. J. D. M. Olsson, L. Eriksson, M. Lahmann, S. Oscarson, J. Org. Chem. 2008, 73, 7181-7188.
36. C.-T. Ren, Y.-H. Tsai, Y.-L. Yang, W. Zou, S.-H. Wu, J. Org. Chem. 2007, 72, 5427-5430.
37. M.-Y. Chen, L. N. Patkar, M.-D. Jan, A. S.-Y. Lee, C.-C. Lin, Tetrahedron Lett. 2004, 45, 635-639.
38. P. Wei, R. J. Kerns, J. Org. Chem. 2005, 70, 4195-4198.
39. K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Carbohydr. Res. 1991, 222, 189-203.
40. G. A. Kraus, B. Roth, J. Org. Chem. 1980, 45, 4825-4830.
41. U. Buwitt-Beckmann, H. Heine, K. H. Wiesmüller, G. Jung, R. Brock, A. J. Ulmer, FEBS J. 2005, 272, 6354-6364
42. U. Buwitt-Beckmann, H. Heine, K. H. Wiesmüller, G. Jung, R. Brock, S. Akira, A. J. Ulmer, J. Biol. Chem. 2005, 281, 9049-9057
43. M. Morr, O. Takeuchi, S. Akira, M. M. Simon, P. F. Mühlradt, Eur. J. Immunol. 2002, 32, 3337-3347.
44. J.-D. Lee, M. Ueno, Y. Miyajima, H. Nakamura, Org. Lett. 2007, 9, 323-326.
45. T. A. Foglia, P. D. Vail, Org. Prep. Proced. Int. 1993, 25, 209-213.
46. S. F. Martin, J. A. Josey, Y. L. Wong, D. W. Dean, J. Org. Chem. 1994, 59, 4805-4820.
47. X. Guo, P. Jiang, H. Fu, Y. Jiang, Y. Zhao, Nucleos. Nucleot. Nucl. 2005, 24, 1325-1331.
48. V. Avramopoulou, S. Antonopoulou, D. Argyropoulos, C. Froussios, C. A. Demopoulos, Int. J. Biochem. Cell Biol. 1997, 29, 767-774.
49. X. Liu, B. Stocker, P. H. Seeberger, J. Am. Chem. Soc. 2006, 128, 3638-3648.