Semisynthesis of Intact Complex-Type Triantennary Oligosaccharides from a Biantennary Oligosaccharide Isolated from a Natural Source by Selective Chemical and Enzymatic Glycosylation

Journal of the American Chemical Society

Volumn 138, Issue 10, 2016, Pages 3461-3468

  Maki, Yuta ^a   Okamoto, Ryo ^a   Izumi, Masayuki ^a   Murase, Takefumi ^b,c   Kajihara, Yasuhiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b YOKOHAMA CITY UNIVERSITY   (Japan)

^c GlyTech   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; OLIGOSACCHARIDE;

CARBOHYDRATE ANALYSIS; CHEMISTRY; GLYCOSYLATION; METABOLISM; SYNTHESIS;

BENZYLIDENE COMPOUNDS; CARBOHYDRATE SEQUENCE; GLYCOSYLATION; OLIGOSACCHARIDES;

EID: 84962546877     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b13098     Document Type: Article

References (36)

1. Essentials of Glycobiology; Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Stanley, P., Bertozzi, C. R., Hart, G. W., Etzler, M. E., Eds.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 2009.
2. Apweiler, R.; Hermjakob, H.; Sharon, N. Biochim. Biophys. Acta, Gen. Subj. 1999, 1473, 4 10.1016/S0304-4165(99)00165-8
3. Lowe, J. B. Cell 2001, 104, 809 10.1016/S0092-8674(01)00277-X
4. Dwek, R. A. Chem. Rev. 1996, 96, 683 10.1021/cr940283b
5. Rudd, P. M.; Dwek, R. A. Crit. Rev. Biochem. Mol. Biol. 1997, 32, 1 10.3109/10409239709085144
6. Boltje, T. J.; Buskas, T.; Boons, G. J. Nat. Chem. 2009, 1, 611 10.1038/nchem.399
7. Guo, J.; Ye, X. S. Molecules 2010, 15, 7235 10.3390/molecules15107235
8. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503 10.1021/cr00020a006
9. Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900 10.1002/anie.200802036
10. Unverzagt, C.; Kajihara, Y. Chem. Soc. Rev. 2013, 42, 4408 10.1039/c3cs35485g
11. Schmaltz, R. M.; Hanson, S. R.; Wong, C.-H. Chem. Rev. 2011, 111, 4259 10.1021/cr200113w
12. Blixt, O.; Head, S.; Mondala, T.; Scanlan, C.; Huflejt, M. E.; Alvarez, R.; Bryan, M. C.; Fazio, F.; Calarese, D.; Stevens, J.; Razi, N.; Stevens, D. J.; Skehel, J. J.; van Die, I.; Burton, D. R.; Wilson, I. A.; Cummings, R.; Bovin, N.; Wong, C. H.; Paulson, J. C. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 17033 10.1073/pnas.0407902101
13. Stevens, J.; Blixt, O.; Paulson, J. C.; Wilson, I. A. Nat. Rev. Microbiol. 2006, 4, 857 10.1038/nrmicro1530
14. Higuchi, M.; Oh-eda, M.; Kuboniwa, H.; Tomonoh, K.; Shimonaka, Y.; Ochi, N. J. Biol. Chem. 1992, 267, 7703
15. Dennis, J. W.; Laferte, S.; Waghorne, C.; Breitman, M. L.; Kerbel, R. S. Science 1987, 236, 582 10.1126/science.2953071
16. Walczak, M. A.; Hayashida, J.; Danishefsky, S. J. J. Am. Chem. Soc. 2013, 135, 4700 10.1021/ja401385v
17. Walczak, M. A.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 16430 10.1021/ja307628w
18. Shivatare, S. S.; Chang, S. H.; Tsai, T. I.; Ren, C. T.; Chuang, H. Y.; Hsu, L.; Lin, C. W.; Li, S. T.; Wu, C. Y.; Wong, C. H. J. Am. Chem. Soc. 2013, 135, 15382 10.1021/ja409097c
19. Wang, Z.; Chinoy, Z. S.; Ambre, S. G.; Peng, W.; McBride, R.; de Vries, R. P.; Glushka, J.; Paulson, J. C.; Boons, G. J. Science 2013, 341, 379 10.1126/science.1236231
20. Unverzagt, C.; Gundel, G.; Eller, S.; Schuberth, R.; Seifert, J.; Weiss, H.; Niemietz, M.; Pischl, M.; Raps, C. Chem.-Eur. J. 2009, 15, 12292 10.1002/chem.200901908
21. Ogawa, T.; Sugimoto, M.; Kitajima, T.; Sadozai, K. K.; Nukada, T. Tetrahedron Lett. 1986, 27, 5739 10.1016/S0040-4039(00)85314-9
22. Wu, B.; Hua, Z.; Warren, J. D.; Ranganathan, K.; Wan, Q.; Chen, G.; Tan, Z.; Chen, J.; Endo, A.; Danishefsky, S. J. Tetrahedron Lett. 2006, 47, 5577 10.1016/j.tetlet.2006.05.086
23. Kajihara, Y.; Suzuki, Y.; Yamamoto, N.; Sasaki, K.; Sakakibara, T.; Juneja, L. R. Chem.-Eur. J. 2004, 10, 971 10.1002/chem.200305115
24. Seko, A.; Koketsu, M.; Nishizono, M.; Enoki, Y.; Ibrahim, H. R.; Juneja, L. R.; Kim, M.; Yamamoto, T. Biochim. Biophys. Acta, Gen. Subj. 1997, 1335, 23 10.1016/S0304-4165(96)00118-3
25. Kirschning, A.; Hahn, F. Angew. Chem., Int. Ed. 2012, 51, 4012 10.1002/anie.201107386
26. Altmann, K.-H.; Gaugaz, F.; Schiess, R. Mol. Diversity 2011, 15, 383 10.1007/s11030-010-9291-0
27. Muir, T. W. Annu. Rev. Biochem. 2003, 72, 249 10.1146/annurev.biochem.72.121801.161900
28. Kumar H. V., R.; Naruchi, K.; Miyoshi, R.; Hinou, H.; Nishimura, S.-I. Org. Lett. 2013, 15, 6278 10.1021/ol403140h
29. Lopin, C.; Jacquinet, J.-C. Angew. Chem., Int. Ed. 2006, 45, 2574 10.1002/anie.200503551
30. Vibert, A.; Lopin-Bon, C.; Jacquinet, J.-C. Chem.-Eur. J. 2009, 15, 9561 10.1002/chem.200900740
31. Kurita, K.; Matsumura, Y.; Takahara, H.; Hatta, K.; Shimojoh, M. Biomacromolecules 2011, 12, 2267 10.1021/bm200353m
32. Laezza, A.; Iadonisi, A.; Castro, C. D.; De Rosa, M.; Schiraldi, C.; Parrilli, M.; Bedini, E. Biomacromolecules 2015, 16, 2237 10.1021/acs.biomac.5b00640
33. Yamamoto, N.; Takayanagi, A.; Sakakibara, T.; Dawson, P. E.; Kajihara, Y. Tetrahedron Lett. 2006, 47, 1341 10.1016/j.tetlet.2005.12.064
34. Kajihara, Y.; Kodama, H.; Wakabayashi, T.; Sato, K.-i.; Hashimoto, H. Carbohydr. Res. 1993, 247, 179 10.1016/0008-6215(93)84251-Z
35. Izumi, M.; Wong, C.-H. Trends Glycosci. Glycotechnol. 2001, 13, 345 10.4052/tigg.13.345
36. Yamamoto, T.; Nakashizuka, M.; Kodama, H.; Kajihara, Y.; Terada, I. J. Biochem. 1996, 120, 104 10.1093/oxfordjournals.jbchem.a021370