Applying pairwise combinations of amino acid mutations for sorting out highly efficient glucosylation tools for chemo-enzymatic synthesis of bacterial oligosaccharides

Journal of the American Chemical Society

Volumn 134, Issue 45, 2012, Pages 18677-18688

  Champion, Elise ^a,b,c   Guérin, Frédéric ^a,b,c,d   Moulis, Claire ^a,b,c   Barbe, Sophie ^a,b,c   Tran, Thu Hoai ^a,b,c,d   Morel, Sandrine ^a,b,c   Descroix, Karine ^e   Monsan, Pierre ^a,b,c   Mourey, Lionel ^a,d   Mulard, Laurence A ^e   Tranier, Samuel ^a,d   Remaud Siméon, Magali ^a,b,c   André, Isabelle ^a,b,c  

^a UNIVERSITÉ PAUL SABATIER   (France)

^b CNRS   (France)

^c UMR792 INGÉNIERIE DES SYSTÈMES BIOLOGIQUES ET DES PROCÉDÉS   (France)

^d INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

^e INSTITUT PASTEUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; CATALYTIC PERFORMANCE; CATALYTIC PROCESS; CATALYTIC RESIDUE; CHEMO-ENZYMATIC SYNTHESIS; DONOR SUBSTRATES; DOUBLE MUTANTS; ENZYME LIBRARIES; GLUCOPYRANOSIDE; GLUCOSYLATION; MOLECULAR DYNAMICS SIMULATIONS; PAIR-WISE COMBINATIONS; PROTEIN DYNAMICS; SATURATION MUTAGENESIS; TRANSGLUCOSIDASE; WILD-TYPE ENZYMES; X-RAY STRUCTURE;

AMINO ACIDS; CARBOHYDRATES; MOLECULAR DYNAMICS; SUGAR (SUCROSE);

ENZYMES;

2 ACETAMIDO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; AMYLOSUCRASE; ENZYME VARIANT; GLUCOPYRANOSIDE; OLIGOSACCHARIDE; SUCRASE; SUCROSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME ISOLATION; ENZYME LOCALIZATION; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SYNTHESIS; GLYCOSYLATION; MOLECULAR DYNAMICS; MOLECULAR LIBRARY; MUTATION; NEISSERIA; NEISSERIA POLYSACCHAREA; NONHUMAN; PROTEIN TARGETING;

AMINO ACIDS; BIOCATALYSIS; ENZYME STABILITY; GENETIC VARIATION; GLUCOSYLTRANSFERASES; GLYCOSYLATION; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; MUTATION; NEISSERIA; OLIGOSACCHARIDES;

EID: 84869448642     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306845b     Document Type: Article

References (46)

1. Niyogi, S. K. J. Microbiol. 2005, 43, 133-43
2. Foster, R. A.; Carlin, N. I.; Majcher, M.; Tabor, H.; Ng, L. K.; Widmalm, G. Carbohydr. Res. 2011, 346, 872-6
3. Passwell, J. H.; Harlev, E.; Ashkenazi, S.; Chu, C.; Miron, D.; Ramon, R.; Farzan, N.; Shiloach, J.; Bryla, D. A.; Majadly, F.; Roberson, R.; Robbins, J. B.; Schneerson, R. Infect. Immun. 2001, 69, 1351-7
4. Passwell, J. H.; Ashkenzi, S.; Banet-Levi, Y.; Ramon-Saraf, R.; Farzam, N.; Lerner-Geva, L.; Even-Nir, H.; Yerushalmi, B.; Chu, C.; Shiloach, J.; Robbins, J. B.; Schneerson, R. Vaccine 2010, 28, 2231-5
5. Belot, F.; Guerreiro, C.; Baleux, F.; Mulard, L. A. Chemistry 2005, 11, 1625-35
6. Phalipon, A.; Tanguy, M.; Grandjean, C.; Guerreiro, C.; Belot, F.; Cohen, D.; Sansonetti, P. J.; Mulard, L. A. J. Immunol. 2009, 182, 2241-7
7. Said Hassane, F.; Phalipon, A.; Tanguy, M.; Guerreiro, C.; Belot, F.; Frisch, B.; Mulard, L. A.; Schuber, F. Vaccine 2009, 27, 5419-26
8. Lindberg, A. A.; Karnell, A.; Weintraub, A. Rev. Infect. Dis. 1991, 13, S279-84
9. Champion, E.; André, I.; Mulard, L. A.; Monsan, P.; Remaud-Siméon, M.; Morel, S. J. Carbohydr. Chem. 2008, 28, 142-160
10. Champion, E.; André, I.; Moulis, C.; Boutet, J.; Descroix, K.; Morel, S.; Monsan, P.; Mulard, L. A.; Remaud-Siméon, M. J. Am. Chem. Soc. 2009, 131, 7379-89
11. André, I.; Potocki-Véronèse, G.; More, S.; Monsan, P.; Remaud-Siméon, M. Top. Curr. Chem. 2010, 294, 25-48
12. Neylon, C. Nucleic Acids Res. 2004, 32, 1448-59
13. Yuan, L.; Kurek, I.; English, J.; Keenan, R. Microbiol. Mol. Biol. Rev. 2005, 69, 373-92
14. Monchois, V.; Willemot, R. M.; Monsan, P. FEMS Microbiol. Rev. 1999, 23, 131-51
15. Henrissat, B.; Davies, G. Curr. Opin. Struct. Biol. 1997, 7, 637-44
16. Coutinho, P. M.; Henrissat, B. Carbohydrate-active enzymes: an integrated database approach. In Recent Advances in Carbohydrate Bioengineering; Gilbert, H. J.; Davies, G.; Henrissat, B.; Svensson, B., Eds.; The Royal Society of Chemistry: Cambridge, 1999; pp 3-12.
17. Reetz, M. T.; Wang, L. W.; Bocola, M. Angew. Chem., Int. Ed. 2006, 45, 1236-41
18. Reetz, M. T.; Carballeira, J. D. Nat. Protoc. 2007, 2, 891-903
19. De Montalk, G. P.; Remaud-Siméon, M.; Willemot, R. M.; Planchot, V.; Monsan, P. J. Bacteriol. 1999, 181, 375-81
20. Ghosh, M.; Dulina, R. G.; Kakarla, R.; Sofia, M. J. J. Org. Chem. 2000, 65, 8387-90
21. Champion, E.; Moulis, C.; Morel, S.; Mulard, L. A.; Monsan, P.; Remaud-Siméon, M.; André, I. ChemCatChem 2010, 2, 969-975
22. Sumner, J.; Howell, S. A. J. Biol. Chem. 1935, 108, 51-54
23. Skov, L. K.; Mirza, O.; Henriksen, A.; Potocki de Montalk, G.; Remaud-Siméon, M.; Sarabal, P.; Willemot, R. M.; Monsan, P.; Gajhede, M. Acta Crystallogr., Sect. D 2000, 56, 203-5
24. Skov, L. K.; Mirza, O.; Henriksen, A.; De Montalk, G. P.; Remaud-Siméon, M.; Sarabal, P.; Willemot, R. M.; Monsan, P.; Gajhede, M. J. Biol. Chem. 2001, 276, 25273-8
25. Battye, T. G.; Kontogiannis, L.; Johnson, O.; Powell, H. R.; Leslie, A. G. Acta Crystallogr., Sect. D 2011, 67, 271-81
26. Evans, P. Acta Crystallogr., Sect. D 2006, 62, 72-82
27. Collaborative Computational Project. Acta Crystallogr., Sect. D 1994, 50, 760-3
28. Potterton, E.; Briggs, P.; Turkenburg, M.; Dodson, E. Acta Crystallogr., Sect. D 2003, 59, 1131-7
29. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D 1997, 53, 240-255
30. Emsley, P.; Cowtan, K. Acta Crystallogr., Sect. D 2004, 60, 2126-32
31. Case, D. A.; Darden, T. E.; Cheatham, I. T. E.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Merz, K. M.; Pearlman, D. A.; Crowley, M.; Walker, R. C.; Zhang, W.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Wong, K. F.; Paesani, F.; Wu, X.; Brozell, S.; Tsui, V.; Gohlke, H.; Yang, L.; Tan, C.; Mongan, J.; Hornak, V.; Cui, G.; Beroza, P.; Mathews, D. H.; Schafmeister, C.; Ross, W. S.; Kollman, P. A. AMBER 9; University of California: San Francisco, CA, 2006.
32. Duan, Y.; Wu, C.; Chowdhury, S.; Lee, M. C.; Xiong, G.; Zhang, W.; Yang, R.; Cieplak, P.; Luo, R.; Lee, T.; Caldwell, J.; Wang, J.; Kollman, P. J. Comput. Chem. 2003, 24, 1999-2012
33. Lee, M. C.; Duan, Y. Proteins 2004, 55, 620-34
34. Kirschner, K. N.; Yongye, A. B.; Tschampel, S. M.; Gonzalez-Outeirino, J.; Daniels, C. R.; Foley, B. L.; Woods, R. J. J. Comput. Chem. 2008, 29, 622-55
35. Pastor, R. W.; Brooks, B. R.; Szabo, A. Mol. Phys. 1988, 65, 1409-1419
36. Berendsen, H. J.; Postma, J. P.; Van Gunsteren, W. F.; Di Nola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684
37. Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. J. Chem. Phys. 1995, 103, 8577-8593
38. Ryckaert, J.-P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341
39. Niesen, F. H.; Berglund, H.; Vedadi, M. Nat. Protoc. 2007, 2, 2212-21
40. Skov, L. K.; Mirza, O.; Sprogoe, D.; Dar, I.; Remaud-Siméon, M.; Albenne, C.; Monsan, P.; Gajhede, M. J. Biol. Chem. 2002, 277, 47741-7
41. Mirza, O.; Skov, L. K.; Remaud-Siméon, M.; Potocki de Montalk, G.; Albenne, C.; Monsan, P.; Gajhede, M. Biochemistry 2001, 40, 9032-9
42. Aghajari, N.; Feller, G.; Gerday, C.; Haser, R. Protein Sci. 2002, 11, 1435-41
43. Davies, G. J.; Wilson, K. S.; Henrissat, B. Biochem. J. 1997, 321, 557-9
44. Cortés, J.; Siméon, T.; Remaud-Siméon, M.; Tran, V. J. Comput. Chem. 2004, 25, 956-967
45. Albenne, C.; Skov, L.; Tran, V.; Gajhede, M.; Monsan, P.; Remaud-Simeon, M.; André-Leroux, G. Proteins 2007, 66, 118-26
46. Potocki de Montalk, G.; Remaud-Siméon, M.; Willemot, R. M.; Sarcabal, P.; Planchot, V.; Monsan, P. FEBS Lett. 2000, 471, 219-23