Chemoenzymatic Assembly of Bacterial Glycoconjugates for Site-Specific Orthogonal Labeling

Journal of the American Chemical Society

Volumn 137, Issue 39, 2015, Pages 12446-12449

  Lukose, Vinita ^a   Whitworth, Garrett ^a   Guan, Ziqiang ^b   Imperiali, Barbara ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELL MEMBRANES; POLYSACCHARIDES;

BIOLOGICAL INTERACTIONS; CAMPYLOBACTER JEJUNI; CHEMOENZYMATIC APPROACHES; HEPTASACCHARIDES; HOST-PATHOGEN INTERACTIONS; IN-VITRO ANALYSIS; ORTHOGONAL REACTION; PROTEIN GLYCOSYLATION;

CARBOHYDRATES;

ALKYNE; AZIDE; BACTERIAL ENZYME; COPPER; GLYCAN; GLYCOCONJUGATE; GLYCOPEPTIDE; GLYCOSYLTRANSFERASE; N ACETYLGALACTOSAMINE; URIDINE DIPHOSPHATE SUGAR;

ARTICLE; BIOSYNTHESIS; CAMPYLOBACTER JEJUNI; CARBOHYDRATE ANALYSIS; CELL SURFACE; CONJUGATION; CYCLOADDITION; ENZYME ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOST PATHOGEN INTERACTION; IN VITRO STUDY; LIQUID LIQUID EXTRACTION; MASS SPECTROMETRY; NONHUMAN; PROTEIN ASSEMBLY; PROTEIN GLYCOSYLATION; SCINTILLATION COUNTING; ENZYMOLOGY; GLYCOSYLATION; HUMAN; METABOLISM; SYNTHESIS;

CAMPYLOBACTER JEJUNI; CARBOHYDRATE SEQUENCE; GLYCOCONJUGATES; GLYCOSYLATION; HOST-PATHOGEN INTERACTIONS; HUMANS;

EID: 84943567162     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b07146     Document Type: Article

References (34)

1. Varki, A. Glycobiology 1993, 3, 97-130 10.1093/glycob/3.2.97
2. Benz, I.; Schmidt, M. A. Mol. Microbiol. 2002, 45, 267-276 10.1046/j.1365-2958.2002.03030.x
3. Tytgat, H. L.; Lebeer, S. Microbiol. Mol. Biol. Rev. 2014, 78, 372-417 10.1128/MMBR.00007-14
4. Comstock, L. E. Cell Host Microbe 2009, 5, 522-526 10.1016/j.chom.2009.05.010
5. Nothaft, H.; Szymanski, C. M. Nat. Rev. Microbiol. 2010, 8, 765-778 10.1038/nrmicro2383
6. Tra, V. N.; Dube, D. H. Chem. Commun. (Cambridge, U. K.) 2014, 50, 4659-4673 10.1039/c4cc00660g
7. Stowell, S. R.; Arthur, C. M.; McBride, R.; Berger, O.; Razi, N.; Heimburg-Molinaro, J.; Rodrigues, L. C.; Gourdine, J. P.; Noll, A. J.; von Gunten, S.; Smith, D. F.; Knirel, Y. A.; Paulson, J. C.; Cummings, R. D. Nat. Chem. Biol. 2014, 10, 470-476 10.1038/nchembio.1525
8. Li, Q.; Li, Z.; Duan, X.; Yi, W. J. Am. Chem. Soc. 2014, 136, 12536-12539 10.1021/ja5054225
9. Astronomo, R. D.; Burton, D. R. Nat. Rev. Drug Discovery 2010, 9, 308-324 10.1038/nrd3012
10. Szymanski, C. M.; Logan, S. M.; Linton, D.; Wren, B. W. Trends Microbiol. 2003, 11, 233-238 10.1016/S0966-842X(03)00079-9
11. Hendrixson, R. R.; DiRita, V. J. Mol. Microbiol. 2004, 52, 471-484 10.1111/j.1365-2958.2004.03988.x
12. Karlyshev, A. V.; Everest, P.; Linton, D.; Cawthraw, S.; Newell, D. G.; Wren, B. W. Microbiology 2004, 150, 1957-1964 10.1099/mic.0.26721-0
13. Kelly, J.; Jarrell, H.; Millar, L.; Tessier, L.; Fiori, L. M.; Lau, P. C.; Allan, B.; Szymanski, C. M. J. Bacteriol. 2006, 188, 2427-2434 10.1128/JB.188.7.2427-2434.2006
14. Amin, M. N.; Ishiwata, A.; Ito, Y. Tetrahedron 2007, 63, 8181-8198 10.1016/j.tet.2007.05.126
15. Kumar, M.; Balaji, P. V. Mol. BioSyst. 2011, 7, 1629-1645 10.1039/c0mb00259c
16. Chauhan, J. S.; Bhat, A. H.; Raghava, G. P.; Rao, A. PLoS One 2012, 7, e40155 10.1371/journal.pone.0040155
17. Glover, K. J.; Weerapana, E.; Imperiali, B. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 14255-14259 10.1073/pnas.0507311102
18. Troutman, J. M.; Imperiali, B. Biochemistry 2009, 48, 2807-2816 10.1021/bi802284d
19. Dube, D. H.; Bertozzi, C. R. Curr. Opin Chem. Biol. 2003, 7, 616-625
20. Jaffee, M. B.; Imperiali, B. Biochemistry 2011, 50, 7557-7567 10.1021/bi201018d
21. Swiezewska, E.; Sasak, W.; Mankowski, T.; Jankowski, W.; Vogtman, T.; Krajewska, I.; Hertel, J.; Skoczylas, E.; Chojnacki, T. Acta Biochim Pol 1994, 41, 221-260
22. Watanabe, Y.; Nakamura, T.; Mitsumoto, H. Tetrahedron Lett. 1997, 38, 7407-7410 10.1016/S0040-4039(97)85781-4
23. Olivier, N. B.; Chen, M. M.; Behr, J. R.; Imperiali, B. Biochemistry 2006, 45, 13659-13669 10.1021/bi061456h
24. Wacker, M.; Feldman, M. F.; Callewaert, N.; Kowarik, M.; Clarke, B. R.; Pohl, N. L.; Hernandez, M.; Vines, E. D.; Valvano, M. A.; Whitfield, C.; Aebi, M. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 7088-7093 10.1073/pnas.0509207103
25. Cai, L.; Guan, W.; Kitaoka, M.; Shen, J.; Xia, C.; Chen, W.; Wang, P. G. Chem. Commun. (Cambridge, U. K.) 2009, 2944-2946 10.1039/b904853g
26. Guan, W.; Cai, L.; Wang, P. G. Chem.-Eur. J. 2010, 16, 13343-13345 10.1002/chem.201002315
27. Gennaro, L. A.; Salas-Solano, O. Anal. Chem. 2008, 80, 3838-3845 10.1021/ac800152h
28. Maury, D.; Couderc, F.; Czaplicki, J.; Garrigues, J. C.; Poinsot, V. Biomed. Chromatogr. 2010, 24, 343-346 10.1002/bmc.1299
29. van Sorge, N. M.; Bleumink, N. M.; van Vliet, S. J.; Saeland, E.; van der Pol, W. L.; van Kooyk, Y.; van Putten, J. P. Cell. Microbiol. 2009, 11, 1768-1781 10.1111/j.1462-5822.2009.01370.x
30. Chen, M. M.; Glover, K. J.; Imperiali, B. Biochemistry 2007, 46, 5579-5585 10.1021/bi602633n
31. Liu, F.; Vijayakrishnan, B.; Faridmoayer, A.; Taylor, T. A.; Parsons, T. B.; Bernardes, G. J.; Kowarik, M.; Davis, B. G. J. Am. Chem. Soc. 2014, 136, 566-569 10.1021/ja409409h
32. Hug, I.; Zheng, B.; Reiz, B.; Whittal, R. M.; Fentabil, M. A.; Klassen, J. S.; Feldman, M. F. J. Biol. Chem. 2011, 286, 37887-37894 10.1074/jbc.M111.287755
33. Boyce, M.; Carrico, I. S.; Ganguli, A. S.; Yu, S. H.; Hangauer, M. J.; Hubbard, S. C.; Kohler, J. J.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 3141-3146 10.1073/pnas.1010045108
34. Yu, S. H.; Boyce, M.; Wands, A. M.; Bond, M. R.; Bertozzi, C. R.; Kohler, J. J. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 4834-4839 10.1073/pnas.1114356109