A sialyltransferase mutant with decreased donor hydrolysis and reduced sialidase activities for directly sialylating Lewisx

ACS Chemical Biology

Volumn 7, Issue 7, 2012, Pages 1232-1240

  Sugiarto, Go ^a   Lau, Kam ^a   Qu, Jingyao ^a   Li, Yanhong ^a   Lim, Sunghyuk ^a   Mu, Shengmao ^a   Ames, James B ^a   Fisher, Andrew J ^a   Chen, Xi ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUCOSE; GLYCOCONJUGATE; GLYCOSYLTRANSFERASE; SIALIC ACID; SIALIDASE; SIALYL LEWIS X ANTIGEN; SIALYLTRANSFERASE;

ARTICLE; CATALYST; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DONOR; ENZYME ACTIVITY; ENZYME MECHANISM; GLYCOSYLATION; HYDROLYSIS KINETICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PASTEURELLA MULTOCIDA; PRIORITY JOURNAL; WILD TYPE; X RAY;

ANTIGENS, CD15; CRYSTALLOGRAPHY, X-RAY; ENZYME ACTIVATION; HYDROLYSIS; MUTATION; NEURAMINIDASE; PASTEURELLA MULTOCIDA; SIALYLTRANSFERASES;

PASTEURELLA MULTOCIDA;

EID: 84864148567     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb300125k     Document Type: Article

References (43)

1. Koeller, K. M. and Wong, C. H. (2001) Enzymes for chemical synthesis Nature 409, 232-240
2. Koeller, K. M. and Wong, C. H. (2000) Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies Chem. Rev. 100, 4465-4493
3. Wymer, N. and Toone, E. J. (2000) Enzyme-catalyzed synthesis of carbohydrates Curr. Opin. Chem. Biol. 4, 110-119
4. Weijers, C. A., Franssen, M. C., and Visser, G. M. (2008) Glycosyltransferase-catalyzed synthesis of bioactive oligosaccharides Biotechnol. Adv. 26, 436-456
5. Wakarchuk, W. W., Cunningham, A., Watson, D. C., and Young, N. M. (1998) Role of paired basic residues in the expression of active recombinant galactosyltransferases from the bacterial pathogen Neisseria meningitidis Protein Eng. 11, 295-302
6. Gilbert, M., Bayer, R., Cunningham, A. M., DeFrees, S., Gao, Y., Watson, D. C., Young, N. M., and Wakarchuk, W. W. (1998) The synthesis of sialylated oligosaccharides using a CMP-Neu5Ac synthetase/sialyltransferase fusion Nat. Biotechnol. 16, 769-772
7. Gilbert, M., Cunningham, A. M., Watson, D. C., Martin, A., Richards, J. C., and Wakarchuk, W. W. (1997) Characterization of a recombinant Neisseria meningitidis alpha-2,3-sialyltransferase and its acceptor specificity Eur. J. Biochem. 249, 187-194
8. Williams, G. J., Zhang, C., and Thorson, J. S. (2007) Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution Nat. Chem. Biol. 3, 657-662
9. Gantt, R. W., Goff, R. D., Williams, G. J., and Thorson, J. S. (2008) probing the aglycon promiscuity of an engineered glycosyltransferase Angew. Chem., Int. Ed. 47, 8889-8892
10. Yang, G., Rich, J. R., Gilbert, M., Wakarchuk, W. W., Feng, Y., and Withers, S. G. (2010) Fluorescence activated cell sorting as a general ultra-high-throughput screening method for directed evolution of glycosyltransferases J. Am. Chem. Soc. 132, 10570-10577
11. Yu, H., Chokhawala, H., Karpel, R., Yu, H., Wu, B., Zhang, J., Zhang, Y., Jia, Q., and Chen, X. (2005) A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries J. Am. Chem. Soc. 127, 17618-17619
12. Chokhawala, H. A., Huang, S., Lau, K., Yu, H., Cheng, J., Thon, V., Hurtado-Ziola, N., Guerrero, J. A., Varki, A., and Chen, X. (2008) Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides ACS Chem. Biol. 3, 567-576
13. Cao, H., Li, Y., Lau, K., Muthana, S., Yu, H., Cheng, J., Chokhawala, H. A., Sugiarto, G., Zhang, L., and Chen, X. (2009) Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids Org. Biomol. Chem. 7, 5137-5145
14. Morley, T. J. and Withers, S. G. (2010) Chemoenzymatic synthesis and enzymatic analysis of 8-modified cytidine monophosphate-sialic acid and sialyl lactose derivatives J. Am. Chem. Soc. 132, 9430-9437
15. Yu, H., Huang, S., Chokhawala, H., Sun, M., Zheng, H., and Chen, X. (2006) Highly efficient chemoenzymatic synthesis of naturally occurring and non-natural alpha-2,6-linked sialosides: a P. damsela alpha-2,6- sialyltransferase with extremely flexible donor-substrate specificity Angew. Chem., Int. Ed. 45, 3938-3944
16. Drouillard, S., Mine, T., Kajiwara, H., Yamamoto, T., and Samain, E. (2010) Efficient synthesis of 6′-sialyllactose, 6,6′- disialyllactose, and 6′-KDO-lactose by metabolically engineered E. coli expressing a multifunctional sialyltransferase from the Photobacterium sp. JT-ISH-224 Carbohydr. Res. 345, 1394-1399
17. Ugorski, M. and Laskowska, A. (2002) Sialyl Lewis(a): a tumor-associated carbohydrate antigen involved in adhesion and metastatic potential of cancer cells Acta Biochim. Pol. 49, 303-311
18. Rosen, S. D. (2004) Ligands for L-selectin: homing, inflammation, and beyond Annu. Rev. Immunol. 22, 129-156
19. Sell, S. (1990) Cancer-associated carbohydrates identified by monoclonal antibodies Hum. Pathol. 21, 1003-1019
20. Dube, D. H. and Bertozzi, C. R. (2005) Glycans in cancer and inflammation - potential for therapeutics and diagnostics Nat. Rev. 4, 477-488
21. Hakomori, S. (1991) Possible functions of tumor-associated carbohydrate antigens Curr. Opin. Immunol. 3, 646-653
22. x-related antigen expression in human malignant and nonmalignant colonic tissues Cancer Res. 46, 2627-2632
23. Takada, A., Ohmori, K., Yoneda, T., Tsuyuoka, K., Hasegawa, A., Kiso, M., and Kannagi, R. (1993) Contribution of carbohydrate antigens sialyl Lewis A and sialyl Lewis X to adhesion of human cancer cells to vascular endothelium Cancer Res. 53, 354-361
24. Ravindranath, M. H., Kelley, M. C., Jones, R. C., Amiri, A. A., Bauer, P. M., and Morton, D. L. (1998) Ratio of IgG:IgM antibodies to sialyl Lewis(x) and GM3 correlates with tumor growth after immunization with melanoma-cell vaccine with different adjuvants in mice Int. J. Cancer 75, 117-124
25. x Glycobiology 21, 387-396
26. Chen, X. and Varki, A. (2010) Advances in the biology and chemistry of sialic acids ACS Chem. Biol. 5, 163-176
27. Jackson, R. J., Hall, D. F., and Kerr, P. J. (1999) Myxoma virus encodes an alpha2,3-sialyltransferase that enhances virulence J. Virol. 73, 2376-2384
28. Sujino, K., Uchiyama, T., Hindsgaul, O., Seto, N. O. L., Wakarchuk, W., and Palcic, M. M. (2000) Enzymatic synthesis of oligosaccharide analogues: Evaluation of UDP-Gal analogues as donors for three retaining R-galactosyltransferases J. Am. Chem. Soc. 122, 1261-1269
29. Ni, L., Sun, M., Yu, H., Chokhawala, H., Chen, X., and Fisher, A. J. (2006) Cytidine 5′-monophosphate (CMP)-induced structural changes in a multifunctional sialyltransferase from Pasteurella multocida Biochemistry 45, 2139-2148
30. Ni, L., Chokhawala, H. A., Cao, H., Henning, R., Ng, L., Huang, S., Yu, H., Chen, X., and Fisher, A. J. (2007) Crystal structures of Pasteurella multocida sialyltransferase complexes with acceptor and donor analogues reveal substrate binding sites and catalytic mechanism Biochemistry 46, 6288-6298
31. Sugiarto, G., Lau, K., Li, Y., Khedri, Z., Yu, H., Le, D.-T., and Chen, X. (2011) Decreasing the sialidase activity of multifunctional Pasteurella multocida α2-3-sialyltransferase 1 (PmST1) by site-directed mutagenesis Mol. Biosyst. 7, 3021-3027
32. Zhang, L., Lau, K., Cheng, J., Yu, H., Li, Y., Sugiarto, G., Huang, S., Ding, L., Thon, V., Wang, P. G., and Chen, X. (2010) Helicobacter hepaticus Hh0072 gene encodes a novel alpha1-3-fucosyltransferase belonging to CAZy GT11 family Glycobiology 20, 1077-1088
33. Chiu, C. P., Watts, A. G., Lairson, L. L., Gilbert, M., Lim, D., Wakarchuk, W. W., Withers, S. G., and Strynadka, N. C. (2004) Structural analysis of the sialyltransferase CstII from Campylobacter jejuni in complex with a substrate analog Nat. Struct. Mol. Biol. 11, 163-170
34. Chiu, C. P., Lairson, L. L., Gilbert, M., Wakarchuk, W. W., Withers, S. G., and Strynadka, N. C. (2007) Structural analysis of the alpha-2,3- sialyltransferase Cst-I from Campylobacter jejuni in apo and substrate-analogue bound forms Biochemistry 46, 7196-7204
35. Soya, N., Shoemaker, G. K., Palcic, M. M., and Klassen, J. S. (2009) Comparative study of substrate and product binding to the human ABO(H) blood group glycosyltransferses Glycobiology 19, 1224-1234
36. Sindhuwinata, N., Munoz, E., Munoz, F. J., Palcic, M. M., Peters, H., and Peters, T. (2010) Binding of an acceptor substrate analog enhances the enzymatic activity of human blood group B galactosyltransferase Glycobiology 20, 718-723
37. Moustafa, I., Connaris, H., Taylor, M., Zaitsev, V., Wilson, J. C., Kiefel, M. J., von Itzstein, M., and Taylor, G. (2004) Sialic acid recognition by Vibrio cholerae neuraminidase J. Biol. Chem. 279, 40819-40826
38. Jaques, L. W., Brown, E. B., Barrett, J. M., Brey, W. S., Jr., and Weltner, W., Jr. (1977) Sialic acid. A calcium-binding carbohydrate J. Biol. Chem. 252, 4533-4538
39. Severi, E., Muller, A., Potts, J. R., Leech, A., Williamson, D., Wilson, K. S., and Thomas, G. H. (2008) Sialic acid mutarotation is catalyzed by the Escherichia coli beta-propeller protein YjhT J. Biol. Chem. 283, 4841-4849
40. Yu, H., Yu, H., Karpel, R., and Chen, X. (2004) Chemoenzymatic synthesis of CMP-sialic acid derivatives by a one-pot two-enzyme system: comparison of substrate flexibility of three microbial CMP-sialic acid synthetases Bioorg. Med. Chem. 12, 6427-6435
41. Li, Y., Yu, H., Cao, H., Lau, K., Muthana, S., Tiwari, V. K., Son, B., and Chen, X. (2008) Pasteurella multocida sialic acid aldolase: a promising biocatalyst Appl. Microbiol. Biotechnol. 79, 963-970
42. Yi, W., Liu, X., Li, Y., Li, J., Xia, C., Zhou, G., Zhang, W., Zhao, W., Chen, X., and Wang, P. G. (2009) Remodeling bacterial polysaccharides by metabolic pathway engineering Proc. Natl. Acad. Sci. U.S.A. 106, 4207-4212
43. Kajihara, Y., Kamiyama, D., Yamamoto, N., Sakakibara, T., Izumi, M., and Hashimoto, H. (2004) Synthesis of 2-[(2-pyridyl)amino]ethyl beta-D-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl beta-D-lactosaminide Carbohydr. Res. 339, 1545-1550