Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5196-5204

  Hoang, Kim Le Mai ^a   Bai, Yaguang ^a   Ge, Xin ^a   Liu, Xue Wei ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL COMPOUNDS;

ALKYLGLYCOSIDES; COMPUTATIONAL CALCULATIONS; GLYCOCONJUGATES; GLYCOSYLATION REACTIONS; NATIVE CHEMICAL LIGATION; STEREO-SELECTIVE; STEREOSPECIFIC; STEREOSPECIFIC MANNER;

SULFUR COMPOUNDS;

GLYCOCONJUGATE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPUTATIONAL FLUID DYNAMICS; CONFORMATION; GLYCOSYLATION; NATIVE CHEMICAL LIGATION; STEREOSPECIFICITY; SYNTHESIS;

EID: 84879293775     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400020q     Document Type: Article

References (36)

1. Varki, A. Glycobiology 1993, 3, 97-130
2. Dwek, R. A. Chem. Rev. 1996, 96, 683-720
3. Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370-2376
4. Bradbury, E. J.; Moon, L. D. F.; Popat, R. J.; King, V. R.; Bennett, G. S.; Patel, P. N.; Fawcett, J. W.; MacMahon, S. B. Nature 2002, 416, 636-640
5. Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marthet, J. In Essentials of Glycobiology, 2 nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, 2009.
6. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4493
7. Demchenko, A. V. In Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance; Wiley-VCH: New York, 2008.
8. Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900-1934
9. Ishiwata, A.; Lee, Y. J.; Ito, Y. Org. Biomol. Chem. 2010, 8, 3596-3608
10. Cumpstey, I. Carbohydr. Res. 2008, 343, 1553-1573
11. Dawson, P. E.; Muir, T. W.; Lewis, I. C.; Kent, S. B. Science 1994, 266, 776-778
12. Dawson, P. E.; Kent, S. B. Annu. Rev. Biochem. 2000, 69, 923-960
13. Hofmann, R. M.; Muir, T. W. Curr. Opin. Biotech. 2002, 13, 297-303
14. Fang, G. M.; Li, Y. M.; Shen, F.; Huang, Y. C.; Li, J. B.; Lin, Y.; Cui, H. K.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 7645-7649
15. Pasunooti, K. K.; Yang, R.; Vedachalam, S.; Liu, X.-W. Bioorg. Med. Chem. Lett. 2009, 19, 6268-6271
16. Yang, R.; Pasunooti, K. K.; Liu, X.-W. J. Am. Chem. Soc. 2009, 131, 13592-13593
17. Yang, R.; Pasunooti, K. K.; Liu, X.-W. Chem. Commun. 2010, 46, 7199-7201
18. Brown, D. S.; Ley, S. V. Tetrahedron Lett. 1988, 29, 4869-4872
19. Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308
20. Brown, D. S.; Ley, S. V. Tetrahedron Lett. 1988, 29, 4873-4876
21. Bols, M.; Hansen, H. Chem. Lett. 1994, 1049-1052
22. Crich, D.; Sharma, I. J. Org. Chem. 2010, 75, 8383-8391
23. Kim, K. S.; Suk, D.-H. Trends Glycosci. Glycotechnol. 2011, 2353-2366
24. Krumper, J. R.; Salamant, W. A.; Woerpel, K. A. J. Org. Chem. 2009, 74, 8039
25. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79-90 and references therein
26. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173-200
27. Ishiwata, A.; Munemura, Y.; Ito, Y. Tetrahedron 2008, 64, 92-102
28. Schmidt, R. R.; Behrendt, M.; Toepfer, A. Synlett 1990, 694-696
29. Satoh, H.; Hansen, H. S.; Manabe, S.; van Gunsteren, W. F.; Hünenberger, P. H. J. Chem. Theory Comput. 2010, 6, 1783-1797
30. Collins, P. M.; Ferrier, R. J. Monosaccharides; J. Wiley & Sons: Chichester, 1995; p 63.
31. Cumpstey, I. Org. Biomol. Chem. 2012, 10, 2503-2508
32. Gonçalo, J. L. B.; David, P. G.; Benjamin, G. D. Angew. Chem., Int. Ed. 2006, 45, 4007-4011
33. Zhu, X. Tetrahedron Lett. 2006, 47, 7935-7938
34. Nieddu, G.; Giacomelli, G. Synthesis 2008, 24, 3937-3940
35. Nicola, F.; Balakumar, V.; Julia, R. K.; Benjamin, G. D. Angew. Chem., Int. Ed. 2009, 48, 7798-7802
36. Dere, R. T.; Kumar, A.; Schmidt, R. R. J. Org. Chem. 2011, 76, 7539-7545