Total Synthesis of Legionaminic Acid as Basis for Serological Studies

Journal of the American Chemical Society

Volumn 137, Issue 8, 2015, Pages 2848-2851

  Matthies, Stefan ^a,b   Stallforth, Pierre ^a,c   Seeberger, Peter H ^a,b  

^a MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c HANS KNÖLL INSTITUTE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ANTIBODIES; GLUCOSE; ORGANOMETALLICS; PROBES; STEREOCHEMISTRY; STEREOSELECTIVITY;

BACTERIAL PATHOGENS; BIOLOGICAL PROBES; CAUSATIVE AGENTS; GLYCAN MICROARRAYS; LEGIONELLA PNEUMOPHILA; MULTI-COMPONENT REACTIONS; STEREOSELECTIVE REACTIONS; STEREOSELECTIVE SYNTHESIS;

SYNTHESIS (CHEMICAL);

GLYCAN; LEGIONAMINIC ACID; MONOSACCHARIDE; UNCLASSIFIED DRUG; 5,7-DIACETAMIDO-8-O-ACETYL-3,5,7,9-TETRADEOXY-GLYCERO-TALO-NONULOSONIC ACID; GLYCOSIDE; SIALIC ACID DERIVATIVE; THREONINE;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; IMMUNE RESPONSE; LEGIONELLA PNEUMOPHILA; MICROARRAY ANALYSIS; SEROLOGY; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; HUMAN; IMMUNOLOGY; PROCEDURES; STEREOISOMERISM;

CHEMISTRY TECHNIQUES, SYNTHETIC; GLYCOSIDES; HUMANS; MICROARRAY ANALYSIS; SEROLOGIC TESTS; SIALIC ACIDS; STEREOISOMERISM; THREONINE;

EID: 84929192305     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b00455     Document Type: Article

References (54)

1. Varki, A.; Cummings, R. D.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E. Essentials of Glycobiology, 2 nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 2009.
2. Mühlenhoff, M.; Eckhardt, M.; Gerardy-Schahn, R. Curr. Opin. Struct. Biol. 1998, 8, 558
3. Zunk, M.; Kiefel, M. J. RSC Adv. 2014, 4, 3413
4. Knirel, Y. A.; Shashkov, A. S.; Tsvetkov, Y. E.; Jansson, P.-E.; Zähringer, U. In Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed.; Academic Press: Waltham, MA, 2003; Vol. 58, p 371.
5. Cazalet, C.; Jarraud, S.; Ghavi-Helm, Y.; Kunst, F.; Glaser, P.; Etienne, J.; Buchrieser, C. Genome Res. 2008, 18, 431
6. Kooistra, O.; Herfurth, L.; Lüneberg, E.; Frosch, M.; Peters, T.; Zähringer, U. Eur. J. Biochem. 2002, 269, 573
7. Mas Pons, J.; Dumont, A.; Sautejeau, G.; Fugier, E.; Baron, A.; Dukan, S.; Vauzeilles, B. Angew. Chem., Int. Ed. 2014, 53, 1275
8. Tsvetkov, Y. E.; Shashkov, A. S.; Knirel, Y. A.; Zähringer, U. Carbohydr. Res. 2001, 331, 233
9. Vinogradov, E.; MacLean, L.; Xu, H. H.; Chen, W. Carbohydr. Res. 2014, 390, 42
10. Filatov, A. V.; Wang, M.; Wang, W.; Perepelov, A. V.; Shashkov, A. S.; Wang, L.; Knirel, Y. A. Carbohydr. Res. 2014, 392, 21
11. MacLean, L. L.; Vinogradov, E.; Pagotto, F.; Perry, M. B. Carbohydr. Res. 2011, 346, 2589
12. Tsvetkov, Y. E.; Shashkov, A. S.; Knirel, Y. A.; Zähringer, U. Carbohydr. Res. 2001, 335, 221
13. Glaze, P. A.; Watson, D. C.; Young, N. M.; Tanner, M. E. Biochemistry 2008, 47, 3272
14. Watson, D. C.; Leclerc, S.; Wakarchuk, W. W.; Young, N. M. Glycobiology 2011, 21, 99
15. Schumann, B.; Anish, C.; Pereira, C. L.; Seeberger, P. H. In Biotherapeutics: Recent Developments Using Chemical and Molecular Biology; The Royal Society of Chemistry: Cambridge, UK, 2013; p 68.
16. Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046
17. Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415
18. Vogel, P. In The Organic Chemistry of Sugars; Levy, D. E.; Fügedi, P., Eds.; CRC Press: Boca Raton, FL, 2005.
19. Kirschning, A.; Jesberger, M.; Schöning, K.-U. Synthesis 2001, 507
20. Martin, S. F.; Zinke, P. W. J. Am. Chem. Soc. 1989, 111, 2311
21. Aljahdali, A. Z.; Shi, P.; Zhong, Y.; ODoherty, G. A. Adv. Carbohydr. Chem. Biochem. 2013, 69, 55
22. Guo, H.; ODoherty, G. A. J. Org. Chem. 2008, 73, 5211
23. Yu, X.; ODoherty, G. In Chemical Glycobiology; American Chemical Society: Washington, DC, 2008; Vol. 990, p 3.
24. Brasholz, M.; Reissig, H.-U. Angew. Chem., Int. Ed. 2007, 46, 1634
25. Leonori, D.; Seeberger, P. H. Beilstein J. Org. Chem. 2013, 9, 332
26. Leonori, D.; Seeberger, P. H. Org. Lett. 2012, 14, 4954
27. Stallforth, P.; Matthies, S.; Adibekian, A.; Gillingham, D. G.; Hilvert, D.; Seeberger, P. H. Chem. Commun. 2012, 48, 11987
28. Liang, X.; Lee, C.-J.; Chen, X.; Chung, H. S.; Zeng, D.; Raetz, C. R. H.; Li, Y.; Zhou, P.; Toone, E. J. Bioorg. Med. Chem. 2011, 19, 852
29. Szechner, B.; Achmatowicz, O.; Galdecki, Z.; Fruzinski, A. Tetrahedron 1994, 50, 7611
30. Kasai, M.; Ziffer, H. J. Org. Chem. 1983, 48, 2346
31. Watanabe, A.; Kiyota, N.; Yamasaki, T.; Tanda, K.; Miyagoe, T.; Sakamoto, M.; Otsuka, M. J. Heterocycl. Chem. 2011, 48, 1132
32. CCDC 1019693 contains the supplementary crystallographic data for this paper. These data can be obtained from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif.
33. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169
34. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798
35. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155
36. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041
37. Lucio Anelli, P.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559
38. Soulé, J.-F.; Mathieu, A.; Norsikian, S.; Beau, J.-M. Org. Lett. 2010, 12, 5322
39. McLean, N. J.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2004, 45, 3
40. Ito, A.; Takahashi, R.; Baba, Y. Chem. Pharm. Bull. 1975, 23, 3081
41. Prakash, G. K. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. Org. Lett. 2000, 2, 3173
42. Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937
43. Pae, A. N.; Cho, Y. S. Curr. Org. Chem. 2002, 6, 715
44. Lee, Y. J.; Kubota, A.; Ishiwata, A.; Ito, Y. Tetrahedron Lett. 2011, 52, 418
45. Cornforth, J. W.; Firth, M. E.; Gottschalk, A. Biochem. J. 1958, 68, 57
46. Boons, G.-J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539
47. Haberman, J. M.; Gin, D. Y. Org. Lett. 2003, 5, 2539
48. de Paz, J. L.; Seeberger, P. H. QSAR Comb. Sci. 2006, 25, 1027
49. Liu, Y.; Palma, A. S.; Feizi, T. Biol. Chem. 2009, 390, 647
50. Park, S.; Gildersleeve, J. C.; Blixt, O.; Shin, I. Chem. Soc. Rev. 2013, 42, 4310
51. Geissner, A.; Anish, C.; Seeberger, P. H. Curr. Opin. Chem. Biol. 2014, 18, 38
52. Goldblatt, D.; Plikaytis, B. D.; Akkoyunlu, M.; Antonello, J.; Ashton, L.; Blake, M.; Burton, R.; Care, R.; Durant, N.; Feavers, I.; Fernsten, P.; Fievet, F.; Giardina, P.; Jansen, K.; Katz, L.; Kierstead, L.; Lee, L.; Lin, J.; Maisonneuve, J.; Nahm, M. H.; Raab, J.; Romero-Steiner, S.; Rose, C.; Schmidt, D.; Stapleton, J.; Carlone, G. M. Clin. Vaccine Immunol. 2011, 18, 1728-1736
53. Holder, P. K.; Maslanka, S. E.; Pais, L. B.; Dykes, J.; Plikaytis, B. D.; Carlone, G. M. Clin. Diagn. Lab. Immunol. 1995, 2, 132
54. Madore, D. V.; Johnson, C. L.; Phipps, D. C.; Myers, M. G.; Eby, R.; Smith, D. H. Pediatrics 1990, 86, 527