Chemical synthesis of N-linked glycans carrying both mannose-6-phosphate and GlcNAc-mannose-6-phosphate motifs

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 8682-8689

  Liu, Yunpeng ^a   Chen, Gong ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE GROUPS; BINDING ANALYSIS; BINDING ELEMENTS; CHEMICAL SYNTHESIS; DEPROTECTION; EUKARYOTIC CELLS; LATE STAGE; N-ACETYLGLUCOSAMINE; N-GLYCANS; N-LINKED GLYCANS;

SYNTHESIS (CHEMICAL);

BENZYL ACETATE; GLYCAN DERIVATIVE; MANNOSE 6 PHOSPHATE;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; PROTEIN DOMAIN; PROTEIN MOTIF; STEREOCHEMISTRY; SYNTHESIS;

ACETYLGLUCOSAMINE; GLYCOPROTEINS; HYDROLASES; MANNOSEPHOSPHATES; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; POLYSACCHARIDES; PROTEIN BINDING; STEREOISOMERISM; SUGAR PHOSPHATES;

EID: 80055100396     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2010999     Document Type: Article

References (23)

1. Ghosh, P.; Dahms, N. M.; Kornfeld, S. Nat. Rev. Mol. Cell Biol. 2003, 4, 202-212
2. Hasilik, A.; Kelin, U.; Waheed, A.; Strecker, G.; von Figura, K. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 7074-7078
3. Kornfeld, S.; Bao, M.; Brewer, K.; Noll, C.; Canfield, W. J. Biol. Chem. 1999, 274, 32778-32785
4. Srivastava, O. P.; Hindsgaul, O. J. Org. Chem. 1987, 52, 2869-2875
5. Franzyk, H.; Christensen, M. K.; Joergensen, R. M.; Meldal, M.; Cordes, H.; Mouritsen, S.; Bock, K. Bioorg. Med. Chem. 1997, 5, 21-40
6. Berkowitz, D. B.; Maiti, G.; Charette, B. D.; Dreis, C. D.; MacDonald, R. G. Org. Lett. 2004, 6, 4921-4924
7. Fei, X.; Connelly, C. M.; MacDonald, R. G.; Berkowitz, D. B. Bioorg. Med. Chem. Lett. 2008, 18, 3085-3089
8. Song, X.; Lasanajak, Y.; Olson, L. J.; Boonen, M.; Dahms, N. M.; Kornfeld, S.; Cummings, R. D.; Smith, D. F. J. Biol. Chem. 2009, 284, 35201-35214
9. Bohnsack, R. N.; Song, X.; Olson, L. J.; Kudo, M.; Gotschall, R. R.; Canfield, W. M.; Cummings, R. D.; Smith, D. F.; Dahms, N. M. J. Biol. Chem. 2009, 284, 35215-35226
10. Chavez, C. A.; Bohnsack, R. N.; Kudo, M.; Gotschall, R. R.; Canfield, W. M.; Dahms, N. M. Biochemistry 2007, 46, 12604-12617
11. Varki, A.; Kornfeld, S. J. Biol. Chem. 1980, 255, 10847-10858
12. Totani, K.; Ihara, Y.; Matsuo, I.; Ito, Y. J. Am. Chem. Soc. 2008, 130, 2101-2107
13. Nagorny, P.; Fasching, B.; Li, X.; Chen, G.; Aussedat, B.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 5792-5799
14. Huang, W.; Li, C.; Li, B.; Umekawa, M.; Yamamoto, K.; Zhang, X.; Wang, L.-X. J. Am. Chem. Soc. 2009, 131, 2214-2223
15. Piontek, C.; Ring, P.; Harjes, O.; Heinlein, C.; Mezzato, S.; Lombana, N.; Pöhner, C.; Püttner, M.; Silva, D. V.; Martin, A.; Schmid, F. X.; Unverzagt, C. Angew. Chem., Int. Ed. 2009, 48, 1936-1940
16. Xue, J.; Guo, Z. J. Am. Chem. Soc. 2003, 125, 16334-16339
17. Jayaprakash, K. N.; Lu, J.; Fraser-Reid, B. Angew. Chem., Int. Ed. 2005, 44, 5894-5898
18. Liu, X.; Kwon, Y.-U.; Seeberger, P. H. J. Am. Chem. Soc. 2005, 127, 5004-5005
19. Liu, Y.; Chan, Y. M.; Wu, J.; Chen, C.; Benesi, A.; Hu, J.; Wang, Y.; Chen, G. ChemBioChem 2011, 12, 685-690
20. Majumdar, D.; Elsayed, G. A.; Buskas, T.; Boons, G. J. J. Org. Chem. 2005, 70, 1691-1697
21. Shangguan, N.; Katukojvala, S.; Greenberg, R.; Williams, L. J. J. Am. Chem. Soc. 2003, 125, 7754-7755
22. Ali, A.; Vishwakarma, R. A. Tetrahedron Lett. 2000, 66, 4357-4369
23. Shangguan, N.; Katukojvala, S.; Greenberg, R.; Williams, L. J. J. Am. Chem. Soc. 2003, 125, 7754-7755