Structure-based engineering of E. coli galactokinase as a first step toward in vivo glycorandomization

Chemistry and Biology

Volumn 12, Issue 6, 2005, Pages 657-664

  Yang, Jie ^a   Fu, Xun ^a   Liao, Jianchun ^a   Liu, Lesley ^a   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESCHERICHIA COLI; PYRONIA TITHONUS;

CARBOHYDRATE; GALACTOKINASE;

ARTICLE; BINDING SITE; CARBOHYDRATE METABOLISM; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; GLYCOSYLATION; KINETICS; METABOLISM; MUTATION; PHOSPHORYLATION; PROTEIN ENGINEERING; PROTEIN TERTIARY STRUCTURE; RANDOMIZATION;

BINDING SITES; CARBOHYDRATE METABOLISM; CARBOHYDRATES; CATALYSIS; ESCHERICHIA COLI; GALACTOKINASE; GLYCOSYLATION; KINETICS; MODELS, MOLECULAR; MUTATION; PHOSPHORYLATION; PROTEIN ENGINEERING; PROTEIN STRUCTURE, TERTIARY; RANDOM ALLOCATION; SUBSTRATE SPECIFICITY;

EID: 24944496018     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2005.04.009     Document Type: Article

References (35)

1. Weymouth-Wilson, A.C. (1997). The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 14, 99-110.
2. Potier, P. (1999). Nature: a good source of new useful compounds for the health of man, animals and plants... for a long time to come! Actual. Chim. 11, 9-11.
3. Thorson, J.S., and Vogt, T. (2003). Glycosylated natural products. In Glycosylated Natural Products in Carbohydrate-based Drug Discovery, Volume II, C.-W. Wong, ed. (Germany: Wiley-VCH Weinheim), pp. 685-711.
4. Kren, V., and Martinkova, L. (2001). Glycosides in medicine: "the role of glycosidic residue in biological activity". Curr. Med. Chem. 8, 1303-1328.
5. Thorson, J.S., Hosted, T.J., Jr., Jiang, J., Biggins, J.B., and Ahlert, J. (2001). Nature's carbohydrate chemists: the enzymatic glycosylation of bioactive bacterial metabolites. Curr. Org. Chem. 5, 139-167.
6. Fu, X., Albermann, C., Jiang, J., Liao, J., Zhang, C., and Thorson, J.S. (2003). Antibiotic optimization via in vitro glycorandomization. Nat. Biotechnol. 21, 1467-1469.
7. Fu, X., Albermann, C., Zhang, C., and Thorson, J.S. (2004). Diversifying vancomycin via chemoenzymatic strategies. Org. Lett. 7, 1513-1515.
8. Yang, J., Fu, X., Jia, Q., Shen, J., Biggins, J.B., Jiang, J., Zhao, J., Schmidt, J.J., Wang, P.G., and Thorson, J.S. (2003). Studies on the substrate specificity of Escherichia coli galactokinase. Org. Lett. 5, 2223-2226.
9. Hoffmeister, D., Yang, J., Liu, L., and Thorson, J.S. (2003). Creation of the first anomeric D/L-sugar kinase by means of directed evolution. Proc. Natl. Acad. Sci. USA 100, 13184-13189.
10. Hoffmeister, D., and Thorson, J.S. (2004). Mechanistic implications of Escherichia coli galactokinase structure-based engineering. ChemBioChem 5, 989-992.
11. Yang, J., Liu, L., and Thorson, J.S. (2004). Structure-based enhancement of the first anomeric glucokinase. ChemBioChem 5, 992-996.
12. Barton, W.A., Biggins, J.B., Jiang, J., Thorson, J.S., and Nikolov, D.B. (2002). Expanding pyrimidine diphosphosugar libraries via structure-based nucleotidylyltransferase engineering. Proc. Natl. Acad. Sci. USA 99, 13397-13402.
13. Barton, W.A., Biggins, J.B., Lesniak, J., Jeffrey, P.D., Jiang, J., Rajashankar, K.R., Thorson, J.S., and Nikolov, D.B. (2001). Structure, mechanism and engineering of a nucleotidylyltransferase as a first step toward glycorandomization. Nat. Struct. Biol. 8, 545-551.
14. Jiang, J., Albermann, C., and Thorson, J.S. (2003). Application of the nucleotidylyltransferase Ep toward the chemoenzymatic synthesis of dTDP-desosamine analogues. ChemBioChem 4, 443-446.
15. Jiang, J., Biggins, J.B., and Thorson, J.S. (2001). Expanding the pyrimidine diphosphosugar repertoire: the chemoenzymatic synthesis of amino- and acetamidoglucopyranosyl derivatives. Angew. Chem. Int. Ed. Engl. 40, 1502-1505.
16. Jiang, J., Biggins, J.B., and Thorson, J.S. (2000). A general enzymatic method for the synthesis of natural and "unnatural" UDP- and TDP-nucleotide sugars. J. Am. Chem. Soc. 122, 6803-6804.
17. Andreana, P.R., McLellan, J.S., Chen, Y., and Wang, P.G. (2002). Synthesis of 2,6-dideoxysugars via ring-closing olefinic metathesis. Org. Lett. 4, 3875-3878.
18. Northrup, A.B., and MacMillan, D.W. (2004). Two-step synthesis of carbohydrates by selective aldol reactions. Science 305, 1752-1755.
19. Northrup, A.B., Mangion, I.K., Hettche, F., and MacMillan, D.W. (2004). Enantioselective organocatalytic direct aldol reactions of alpha-oxyaldehydes: step one in a two-step synthesis of carbohydrates. Angew. Chem. Int. Ed. Engl. 43, 2152-2154.
20. Albermann, C., Soriano, A., Jiang, J., Vollmer, H., Biggins, J.B., Barton, W.A., Lesniak, J., Nikolov, D.B., and Thorson, J.S. (2003). Substrate specificity of NovM: implications for novobiocin biosynthesis and glycorandomization. Org. Lett. 5, 933-936.
21. Thorson, J.S., Barton, W.A., Hoffmeister, D., Albermann, C., and Nikolov, D.B. (2003). Structure-based enzyme engineering and its impact on in vitro glycorandomization. ChemBioChem 5, 16-25.
22. Yang, J., Hoffmeister, D., Liu, L., Fu, X., and Thorson, J.S. (2004). Natural product glycorandomization. Bioorg. Med. Chem. 12, 1577-1584.
23. Langenhan, J.M., and Thorson, J.S. (2005). Recent carbohydrate-based chemoselective ligation application. Curr. Org. Syn. 2, 59-81.
24. Zhang, J., Kowal, P., Chen, X., and Wang, P.G. (2003). Large-scale synthesis of globotriose derivatives through recombinant E. coli. Org. Biomol. Chem. 1, 3048-3053.
25. Zhang, J., Chen, X., Shao, J., Liu, Z., Kowal, P., Lu, Y., and Wang, P.G. (2003). Synthesis of galactose-containing oligosaccharides through superbeads and superbug approaches: substrate recognition along different biosynthetic pathways. Methods Enzymol. 362, 106-124.
26. Dube, D.H., and Bertozzi, C.R. (2003). Metabolic oligosaccharide engineering as a tool for glycobiology. Curr. Opin. Chem. Biol. 7, 616-625.
27. Saxon, E., and Bertozzi, C.R. (2000). Cell surface engineering by a modified Staudinger reaction. Science 287, 2007-2010.
28. Fuster, M.M., Brown, J.R., Wang, L., and Esko, J.D. (2003). A disaccharide precursor of sialyl Lewis X inhibits metastatic potential of tumor cells. Cancer Res. 63, 2775-2781.
29. Mong, T.K., Lee, L.V., Brown, J.R., Esko, J.D., and Wong, C.H. (2003). Synthesis of N-acetyllactosamine derivatives with variation in the aglycon moiety for the study of inhibition of sialyl Lewis x expression. ChemBioChem 4, 835-840.
30. Shao, J., Hayashi, T., and Wang, P.G. (2003). Enhanced production of alpha-galactosyl epitopes by metabolically engineered Pichia pastoris. Appl. Environ. Microbiol. 69, 5238-5242.
31. Thoden, J.B., and Holden, H.M. (2003). Molecular structure of galactokinase. J. Biol. Chem. 278, 33305-33311.
32. Chatterjee, R., Millard, C.S., Champion, K., Clark, D.P., and Donnelly, M.I. (2001). Mutation of the ptsG gene results in increased production of succinate in fermentation of glucose by Escherichia coli. Appl. Environ. Microbiol. 67, 148-154.
33. Dien, B.S., Nichols, N.N., and Bothast, R.J. (2002). Fermentation of sugar mixtures using Escherichia coli catabolite repression mutants engineered for production of L-lactic acid. J. Ind. Microbiol. Biotechnol. 29, 221-227.
34. Nichols, N.N., Dien, B.S., and Bothast, R.J. (2001). Use of catabolite repression mutants for fermentation of sugar mixtures to ethanol. Appl. Microbiol. Biotechnol. 56, 120-125.
35. Bradford, M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.