Donor substrate promiscuity of bacterial β1-3-N-acetylglucosaminyltransferases and acceptor substrate flexibility of β1-4-galactosyltransferases

Bioorganic and Medicinal Chemistry

Volumn 24, Issue 8, 2016, Pages 1696-1705

  Li, Yanhong ^a   Xue, Mengyang ^a,b   Sheng, Xue ^a,e   Yu, Hai ^a   Zeng, Jie ^a,c   Thon, Vireak ^a,d,f   Chen, Yi ^a   Muthana, Musleh M ^a,g   Wang, Peng G ^b,d   Chen, Xi ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SHANDONG UNIVERSITY   (China)

^c HENAN INSTITUTE OF SCIENCE AND TECHNOLOGY   (China)

^d GEORGIA STATE UNIVERSITY   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^g CHILDREN'S NATIONAL MEDICAL CENTER   (United States)

Author keywords

Acceptor substrate specificity; Carbohydrate; Donor substrate promiscuity; Enzymatic synthesis; Glycosyltransferase; One pot multienzyme

Indexed keywords

BACTERIAL ENZYME; BETA 1 3 N ACETYLGLUCOSAMINYLTRANSFERASE; BETA 1 4 GALACTOSYLTRANSFERASE; CALCIUM ION; GALACTOSYLTRANSFERASE; MAGNESIUM; MANGANESE; MONOSACCHARIDE; OLIGOSACCHARIDE; TRISACCHARIDE; UNCLASSIFIED DRUG; N ACETYLGLUCOSAMINYLTRANSFERASE;

ACCEPTOR SUBSTRATE FLEXIBILITY; AMINO ACID SEQUENCE; ARTICLE; BOVINE; CATALYSIS; COMPARATIVE STUDY; CONTROLLED STUDY; DONOR SUBSTRATE PROMISCUITY; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME SYNTHESIS; HELICOBACTER PYLORI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR CLONING; MOLECULAR DYNAMICS; MOLECULAR LIBRARY; NEISSERIA MENINGITIDIS; ONE POT MULTIENZYME SYNTHESIS; PH; PROTEIN EXPRESSION; SEQUENCE ALIGNMENT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; BIOSYNTHESIS; CHEMISTRY; CONFORMATION; ENZYMOLOGY; METABOLISM;

CARBOHYDRATE CONFORMATION; GALACTOSYLTRANSFERASES; HELICOBACTER PYLORI; N-ACETYLGLUCOSAMINYLTRANSFERASES; NEISSERIA MENINGITIDIS; OLIGOSACCHARIDES; SUBSTRATE SPECIFICITY;

EID: 84960968837     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2016.02.043     Document Type: Article

References (55)

1. W. Peng, J. Pranskevich, C. Nycholat, M. Gilbert, W. Wakarchuk, J.C. Paulson, and N. Razi Glycobiology 22 2012 1453
2. S. Di Virgilio, J. Glushka, K. Moremen, and M. Pierce Glycobiology 9 1999 353
3. K. Naruchi, T. Hamamoto, M. Kurogochi, H. Hinou, H. Shimizu, T. Matsushita, N. Fujitani, H. Kondo, and S. Nishimura J. Org. Chem. 71 2006 9609
4. C.M. Nycholat, W. Peng, R. McBride, A. Antonopoulos, R.P. de Vries, Z. Polonskaya, M.G. Finn, A. Dell, S.M. Haslam, and J.C. Paulson J. Am. Chem. Soc. 135 2013 18280
5. O. Renkonen Cell. Mol. Life Sci. 57 2000 1423
6. D. Vasiliu, N. Razi, Y. Zhang, N. Jacobsen, K. Allin, X. Liu, J. Hoffmann, O. Bohorov, and O. Blixt Carbohydr. Res. 341 2006 1447
7. B. Sauerzapfe, K. Krenek, J. Schmiedel, W.W. Wakarchuk, H. Pelantova, V. Kren, and L. Elling Glycoconjate J. 26 2009 141
8. O. Blixt, and N. Razi Methods Enzymol. 415 2006 137
9. C.M. Nycholat, R. McBride, D.C. Ekiert, R. Xu, J. Rangarajan, W. Peng, N. Razi, M. Gilbert, W. Wakarchuk, I.A. Wilson, and J.C. Paulson Angew. Chem., Int. Ed. 51 2012 4860
10. W.T. Chien, C.F. Liang, C.C. Yu, C.H. Lin, S.P. Li, I. Primadona, Y.J. Chen, K.K. Mong, and C.C. Lin Chem. Commun. 2014 5786
11. K.F. Johnson Glycoconjate J. 16 1999 141
12. H. Yu, K. Lau, V. Thon, C.A. Autran, E. Jantscher-Krenn, M. Xue, Y. Li, G. Sugiarto, J. Qu, S. Mu, L. Ding, L. Bode, and X. Chen Angew. Chem., Int. Ed. 53 2014 6687
13. B. Priem, M. Gilbert, W.W. Wakarchuk, A. Heyraud, and E. Samain Glycobiology 12 2002 235
14. C. Gebus, C. Cottin, M. Randriantsoa, S. Drouillard, and E. Samain Carbohydr. Res. 361 2012 83
15. O. Blixt, I. van Die, T. Norberg, and D.H. van den Eijnden Glycobiology 9 1999 1061
16. A. Togayachi, Y. Kozono, H. Ishida, S. Abe, N. Suzuki, Y. Tsunoda, K. Hagiwara, A. Kuno, T. Ohkura, N. Sato, T. Sato, J. Hirabayashi, Y. Ikehara, K. Tachibana, and H. Narimatsu Proc. Natl. Acad. Sci. U.S.A. 104 2007 15829
17. W. Wakarchuk, A. Martin, M.P. Jennings, E.R. Moxon, and J.C. Richards J. Biol. Chem. 271 1996 19166
18. S.M. Logan, E. Altman, O. Mykytczuk, J.R. Brisson, V. Chandan, M.J. Schur, F. St Michael, A. Masson, S. Leclerc, K. Hiratsuka, N. Smirnova, J. Li, Y. Wu, and W.W. Wakarchuk Glycobiology 15 2005 721
19. W. Guan, L. Ban, L. Cai, L. Li, W. Chen, X. Liu, M. Mrksich, and P.G. Wang Bioorg. Med. Chem. Lett. 21 2011 5025
20. M.M. Palcic Curr. Opin. Chem. Biol. 15 2011 226
21. K. Lau, V. Thon, H. Yu, L. Ding, Y. Chen, M.M. Muthana, D. Wong, R. Huang, and X. Chen Chem. Commun. 2010 6066
22. W.W. Wakarchuk, A. Cunningham, D.C. Watson, and N.M. Young Protein Eng. 11 1998 295
23. J.E. Park, K.Y. Lee, S.I. Do, and S.S. Lee J. Biochem. Mol. Biol. 35 2002 330
24. S.M. Logan, J.W. Conlan, M.A. Monteiro, W.W. Wakarchuk, and E. Altman Mol. Microbiol. 35 2000 1156
25. T. Endo, S. Koizumi, K. Tabata, and A. Ozaki Glycobiology 10 2000 809
26. D.J. Namdjou, H.M. Chen, E. Vinogradov, D. Brochu, S.G. Withers, and W.W. Wakarchuk ChemBioChem 9 2008 1632
27. C. Dumon, C. Bosso, J.P. Utille, A. Heyraud, and E. Samain ChemBioChem 7 2006 359
28. C.H. Wong, R. Wang, and Y. Ichikawa J. Org. Chem. 57 1992 4343
29. M.M. Palcic, O.P. Srivastava, and O. Hindsgaul Carbohydr. Res. 159 1987 315
30. L.J. Berliner, M.E. Davis, K.E. Ebner, T.A. Beyer, and J.E. Bell Mol. Cell. Biochem. 62 1984 37
31. O. Blixt, J. Brown, M.J. Schur, W. Wakarchuk, and J.C. Paulson J. Org. Chem. 66 2001 2442
32. I. Brockhausen, M. Benn, S. Bhat, S. Marone, J.G. Riley, P. Montoya-Peleaz, J.Z. Vlahakis, H. Paulsen, J.S. Schutzbach, and W.A. Szarek Glycoconjate J. 23 2006 525
33. E.E. Boeggeman, P.V. Balaji, N. Sethi, A.S. Masibay, and P.K. Qasba Protein Eng. 6 1993 779
34. B. Ramakrishnan, P.S. Shah, and P.K. Qasba J. Biol. Chem. 276 2001 37665
35. E. Hanada, S. Handa, K. Konno, and T. Yamakawa J. Biochem. 83 1978 85
36. R. Higuchi, K. Inukai, J.X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai Liebigs Ann. Chem. 1993 359
37. Y. Li, H. Yu, Y. Chen, K. Lau, L. Cai, H. Cao, V.K. Tiwari, J. Qu, V. Thon, P.G. Wang, and X. Chen Molecules 16 2011 6396
38. Y. Chen, V. Thon, Y. Li, H. Yu, L. Ding, K. Lau, J. Qu, L. Hie, and X. Chen Chem. Commun. 2011 10815
39. M. Chen, L.L. Chen, Y. Zou, M. Xue, M. Liang, L. Jin, W.Y. Guan, J. Shen, W. Wang, L. Wang, J. Liu, and P.G. Wang Carbohydr. Res. 346 2011 2421
40. M.M. Muthana, J. Qu, Y. Li, L. Zhang, H. Yu, L. Ding, H. Malekan, and X. Chen Chem. Commun. 2012 2728
41. A.S. Donald, and J. Feeney Carbohydr. Res. 178 1988 79
42. T. Urashima, Y. Sun, K. Fukuda, K. Hirayama, E. Taufik, T. Nakamura, T. Saito, J. Merchant, B. Green, and M. Messer Glycoconjate J. 32 2015 361
43. T. Saito, T. Itoh, and S. Adachi Carbohydr. Res. 165 1987 43
44. T. Urashima, T. Saito, J. Nishimura, and H. Ariga Biochem. Biophys. Acta 992 1989 375
45. T. Urashima, Y. Kawai, T. Nakamura, I. Arai, T. Saito, M. Namiki, K. Yamaoka, K. Kawahawa, and M. Messer Comp. Biochem. Physiol. C: Pharmacol. Toxicol. Endocrinol. 124 1999 295
46. K. Fukuda, A. Yamamoto, K. Ganzorig, J. Khuukhenbaatar, A. Senda, T. Saito, and T. Urashima J. Dairy Sci. 93 2010 5572
47. E. Difilippo, H.A. Willems, J.C. Vendrig, J. Fink-Gremmels, H. Gruppen, and H.A. Schols J. Agric. Food Chem. 63 2015 4805
48. C. Kunz, S. Rudloff, W. Schad, and D. Braun Br. J. Nutr. 82 1999 391
49. T. Urashima, S. Fujita, K. Fukuda, T. Nakamura, T. Saito, P. Cowan, and M. Messer Glycoconjate J. 31 2014 387
50. M. Messer, E. Trifonoff, W. Stern, J.G. Collins, and J.H. Bradbury Carbohydr. Res. 83 1980 327
51. T. Urashima, E. Taufik, R. Fukuda, T. Nakamura, K. Fukuda, T. Saito, and M. Messer Glycoconjate J. 30 2013 801
52. L. Zhang, M.M. Muthana, H. Yu, J.B. McArthur, J. Qu, and X. Chen Carbohydr. Res. 419 2016 18
53. M.M. Muthana, J. Qu, M. Xue, T. Klyuchnik, A. Siu, Y. Li, L. Zhang, H. Yu, L. Li, P.G. Wang, and X. Chen Chem. Commun. 2015 4595
54. H. Yu, H. Yu, R. Karpel, and X. Chen Bioorg. Med. Chem. 12 2004 6427
55. L. Zhang, K. Lau, J. Cheng, H. Yu, Y. Li, G. Sugiarto, S. Huang, L. Ding, V. Thon, P.G. Wang, and X. Chen Glycobiology 20 2010 1077