Adherence to Bürgi-Dunitz stereochemical principles requires significant structural rearrangements in Schiff-base formation: Insights from transaldolase complexes

Acta Crystallographica Section D: Biological Crystallography

Volumn 70, Issue 2, 2014, Pages 544-552

  Light, Samuel H ^a,b   Minasov, George ^a,b   Duban, Mark Eugene ^a,c   Anderson, Wayne F ^a,b  

^a Center for Structural Genomics of Infectious Diseases   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c NORTHWESTERN UNIVERSITY   (United States)

Author keywords

B rgi Dunitz angle; imines; induced fit; nucleophiles; pentose phosphate pathway; Schiff bases

Indexed keywords

BACTERIAL PROTEIN; FRUCTOSE 6 PHOSPHATE; FRUCTOSE PHOSPHATE; FRUCTOSE-6-PHOSPHATE; IMINE; NUCLEOPHILE; RECOMBINANT PROTEIN; SCHIFF BASE; SEDOHEPTULOSE 7 PHOSPHATE; SEDOHEPTULOSE 7-PHOSPHATE; SUGAR PHOSPHATE; TRANSALDOLASE;

ARTICLE; BINDING SITE; BIOCATALYSIS; BÜRGI-DUNITZ ANGLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; FRANCISELLA TULARENSIS; GENETICS; INDUCED FIT; METABOLISM; MUTATION; PENTOSE PHOSPHATE CYCLE; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

BÜRGI-DUNITZ ANGLE; IMINES; INDUCED FIT; NUCLEOPHILES; PENTOSE PHOSPHATE PATHWAY; SCHIFF BASES;

BACTERIAL PROTEINS; BINDING SITES; BIOCATALYSIS; CRYSTALLOGRAPHY, X-RAY; ESCHERICHIA COLI; FRANCISELLA TULARENSIS; FRUCTOSEPHOSPHATES; MODELS, MOLECULAR; MUTATION; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; SCHIFF BASES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SUGAR PHOSPHATES; TRANSALDOLASE;

EID: 84894194033     PISSN: 09074449     EISSN: 13990047     Source Type: Journal    
DOI: 10.1107/S1399004713030666     Document Type: Article

References (26)

1. Banki, K. & Perl, A. (1996). FEBS Lett. 378, 161-165.
2. Blom, N. & Sygusch, J. (1997). Nature Struct. Biol. 4, 36-39.
3. Bürgi, H.-B., Dunitz, J., Lehn, J. M. & Wipff, G. (1974). Tetrahedron, 30, 1563-1572.
4. Bürgi, H.-B., Dunitz, J. D. & Shefter, E. (1973). J. Am. Chem. Soc. 95, 5065-5067.
5. Bürgi, H.-B., Lehn, J. M. & Wipff, G. (1974). J. Am. Chem. Soc. 96, 1956-1957.
6. Choi, K. H, Lai, V., Foster, C. E., Morris, A. J., Tolan, D. R. & Allen, K. N. (2006). Biochemistry, 45, 8546-8555.
7. Emsley, P & Cowtan, K. (2004). Acta Cryst. D60, 2126-2132.
8. Fleming, I. (2010). Moleculular Orbitals and Organic Chemical Reactions. Chichester: John Wiley & Sons.
9. Horecker, B. L. & Smyrniotis, P. Z. (1953). J. Am. Chem. Soc. 75, 2021-2022.
10. Jia, J., Huang, W, Schorken, U., Sahm, H, Sprenger, G. A., Lindqvist, Y. & Schneider, G (1996). Structure, 4, 715-724.
11. Laskowski, R. A. & Swindells, M. B. (2011). J. Chem. Inf. Model. 51, 2778-2786.
12. Lehwess-Litzmann, A., Neumann, P., Parthier, C., Lüdtke, S., Golbik, R., Ficner, R. & Tittmann, K. (2011). Nature Chem. Biol. 7, 678-684.
13. Light, S. H., Minasov, G., Shuvalova, L., Duban, M. E., Caffrey, M., Anderson, W. F. & Lavie, A. (2011). J. Biol. Chem. 286, 3531-3539.
14. Light, S. H., Minasov, G., Shuvalova, L., Peterson, S. N., Caffrey, M., Anderson, W. F. & Lavie, A. (2011). Biochemistry, 50, 2357-2363.
15. McCoy, A. J., Grosse-Kunstleve, R. W., Storoni, L. C. & Read, R. J. (2005). Acta Cryst. D61, 458-464.
16. Minor, W., Cymborowski, M., Otwinowski, Z. & Chruszcz, M. (2006). Acta Cryst. D62, 859-866.
17. Miosga, T., Schaaff-Gerstenschlager, I., Franken, E. & Zimmermann, F. K. (1993). Yeast, 9, 1241-1249.
18. Murshudov, G. N., Skubák, P., Lebedev, A. A., Pannu, N. S., Steiner, R. A., Nicholls, R. A., Winn, M. D., Long, F. & Vagin, A. A. (2011). Acta Cryst. D67, 355-367.
19. Reizer, J., Reizer, A. & Saier, M. H. Jr (1995). Microbiology, 141, 961-971.
20. Samland, A. K. & Sprenger, G. A. (2009). Int. J. Biochem. Cell Biol. 41, 1482-1494.
21. Schörken, U., Thorell, S., Schürmann, M., Jia, J., Sprenger, G. A. & Schneider, G. (2001). Eur. J. Biochem. 268, 2408-2415.
22. St-Jean, M. & Sygusch, J. (2007). J. Biol. Chem. 282, 31028-31037.
23. Thorell, S., Gergely, P. Jr, Banki, K., Perl, A. & Schneider, G. (2000). FEBS Lett. 475, 205-208.
24. Thorell, S., Schürmann, M., Sprenger, G. A. & Schneider, G. (2002). J. Mol. Biol. 319, 161-171.
25. Vasileiou, C., Vaezeslami, S., Crist, R. M., Rabago-Smith, M., Geiger, J. H. & Borhan, B. (2007). J. Am. Chem. Soc. 129, 6140-6148.
26. Watt, W. B. & Dean, A. M. (2000). Annu. Rev. Genet. 34, 593-622.