Nucleophilic catalysis of MeON-neoglycoside formation by aniline derivatives

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12189-12193

  Loskot, Steven A ^a   Zhang, Jianjun ^b   Langenhan, Joseph M ^a  

^a SEATTLE UNIVERSITY   (United States)

^b University of Kentucky   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVES; DRUG CANDIDATES; GLYCOPEPTIDES; NATURAL PRODUCTS; NUCLEOPHILIC CATALYSIS; UNCATALYZED REACTIONS;

CHEMISTRY; ORGANIC COMPOUNDS;

ANILINE;

2 AMINO 5 METHOXYBENZOIC ACID; ANILINE DERIVATIVE; BENZOIC ACID DERIVATIVE; FRUCTOSE; GALACTOSE; GLUCOSE; GLYCOSIDE; LACTOSE; N ACETYLGLUCOSAMINE; NEOGLYCOSIDE; NUCLEOPHILE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NEOGLYCOSYLATION; REACTION TIME; SYNTHESIS;

ANILINE COMPOUNDS; CARBOHYDRATE CONFORMATION; CATALYSIS; GLYCOSIDES; HYDROGEN-ION CONCENTRATION;

EID: 84890040828     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401688p     Document Type: Article

References (46)

1. Varki, A. Glycobiology 1993, 3, 97-130
2. Dwek, R. A. Chem. Rev. 1996, 96, 683-720
3. Griffith, B. R.; Langenhan, J. M.; Thorson, J. S. Curr. Opin. Biotechnol. 2005, 16, 622-630
4. Křen, V.; Řezanka, T. FEMS Microbiol. Rev. 2008, 32, 858-889
5. Carbohydrate-Based Vaccines and Immunotherapies; Guo, Z.; Boons, G. -J., Eds.; John Wiley & Sons: Hoboken, 2008.
6. Hart, G. W.; Copeland, R. J. Cell 2010, 143, 672-676
7. Durrant, I. G.; Noble, P.; Spendlove, I. Clin. Exp. Immunol. 2012, 167, 206-215
8. Hanessian, S., Ed. Preparative Carbohydrate Chemistry; Marcel Dekker: New York, 1997.
9. Boons, G.-J., Ed. Carbohydrate Chemistry; Blackie Academic & Professional: New York, 1998
10. Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds. Glycoscience: Chemistry and Chemical Biology I-III; Springer: New York, 2001.
11. Gamblin, D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2009, 109, 131-163
12. Haas, J. W., Jr.; Kadunce, R. E. J. Am. Chem. Soc. 1962, 84, 4910-4913
13. Finch, P.; Merchant, Z. J. Chem. Soc., Perkin Trans. 1 1975, 1682-1686
14. Liu, Y.; Feizi, T.; Campanero-Rhodes, M. A.; Childs, R. A.; Zhang, Y.; Mulloy, B.; Evans, P. G.; Osborn, H. M. I.; Otto, D.; Crocker, P. R.; Chai, W. Chem. Biol. 2007, 14, 847-859
15. Thygesen, M. B.; Sauer, J.; Jensen, K. J. Chem.-Eur. J. 2009, 15, 1649-1660
16. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 826-831
17. Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581-7584
18. Dirksen, A.; Dawson, P. E. Bioconjugate Chem. 2008, 19, 2543-2548
19. Zeng, Y.; Ramya, T. N. C.; Dirksen, A.; Dawson, P. E.; Paulson, J. C. Nature Methods 2009, 6, 207-209
20. Lempens, E. H. M.; Helms, B. A.; Merkx, M.; Meijer, E. W. ChemBioChem 2009, 10, 658-662
21. Rayo, J.; Amara, N.; Krief, P.; Meijler, M. M. J. Am. Chem. Soc. 2011, 133, 7469-7475
22. Guerry, A.; Bernard, J.; Samain, E.; Fleury, E.; Cottaz, S.; Halila, S. Bioconjugate Chem. 2013, 24, 544-549
23. Bindman, N. A.; van der Donk, W. A. J. Am. Chem. Soc. 2013, 135, 10362-10371
24. Thygesen, M. B.; Munch, H.; Sauer, J.; Clo, E.; Jorgensen, M. R.; Hindsgaul, O.; Jensen, K. J. J. Org. Chem. 2010, 75, 1752-1755
25. See also: Wang, W.-J.; Cao, C.-M.; Jin, J.; Wang, X.; Wang, G.-P. Chem. Res. Chin. Univ. 2011, 27, 886-890
26. Peri, F.; Dumy, P.; Mutter, M. Tetrahedron 1998, 54, 12269-12278
27. Langenhan, J. M.; Mullarky, E.; Rogalsky, D. K.; Rohlfing, J. R.; Tjaden, A. E.; Werner, H. M.; Rozal, L. M.; Loskot, S. A. J. Org. Chem. 2013, 78, 1670-1676
28. Langenhan, J. M.; Peters, N. R.; Guzei, I. A.; Hoffman, F. M.; Thorson, J. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305-12310
29. Langenhan, J. M.; Engle, J. M.; Slevin, L. K.; Fay, L. R.; Lucker, R. W.; Smith, K. R.; Endo, M. M. Bioorg. Med. Chem. Lett. 2008, 18, 670-673
30. Goff, R. D.; Thorson, J. S. J. Med. Chem. 2010, 53, 8129-8139
31. Langenhan, J. M.; Endo, M. M.; Engle, J. M.; Fukumoto, L. L.; Rogalsky, D. R.; Slevin, L. K.; Fay, L. R.; Lucker, R. W.; Rohlfing, J. R.; Smith, K. R.; Tjaden, A. E.; Werner, H. M. Carbohydr. Res. 2011, 346, 2663-2676
32. Zhang, J.; Ponomareva, L. V.; Marchillo, K.; Zhou, M.; Andes, D. R.; Thorson, J. S. J. Nat. Prod. 2013, 76, 1627-1636
33. Carrasco, M. R.; Nguyen, M. J.; Burnell, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729
34. Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197
35. Carrasco, M. R.; Brown, R. T. J. Org. Chem. 2003, 68, 8853-8858
36. Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087
37. Filira, F.; Biondi, B.; Biondi, L.; Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063
38. Matsubara, N.; Oiwa, K.; Hohsaka, T.; Sadamoto, R.; Niikura, K.; Fukuhara, N.; Takimoto, A.; Kondo, H.; Nishimura, S.-I. Chem.-Eur. J. 2005, 11, 6974-6981
39. Peri, F.; Nicotra, F. Chem. Commun. 2004, 623-627
40. Peri, F.; Jimenez-Barbero, J.; GarcÌa-Aparicio, V.; Tvaroska, I.; Nicotra, F. Chem.-Eur. J. 2004, 10, 1433-1444
41. Seo, J.; Michaelian, N.; Owens, S. C.; Dashner, S. T.; Wong, A. J.; Barron, A. E.; Carrasco, M. R. Org. Lett. 2009, 11, 5210-5213
42. Crisalli, P.; Kool, E. T. J. Org. Chem. 2013, 78, 1184-1189
43. Crisalli, P.; Kool, E. T. Org. Lett. 2013, 15, 1646-1649
44. Brown, H. C.; McDaniel, D. H.; Hafliger, O. Dissociation Constants. In Determination of Organic Structures by Physical Methods; Braude, E. A.; Nachod, F. C., Eds.; Academic Press: New York, 1955; pp 567-662.
45. Lohse, A.; Martins, R.; Jorgensen, M. R.; Hindsgaul, O. Angew. Chem., Int. Ed. 2006, 45, 4167-4172
46. Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 651-653