Ergothioneine biosynthetic methyltransferase EgtD reveals the structural basis of aromatic amino acid betaine biosynthesis

ChemBioChem

Volumn 16, Issue 1, 2015, Pages 119-125

  Vit, Allegra ^b,c   Misson, Laëtitia ^a   Blankenfeldt, Wulf ^b,c   Seebeck, Florian P ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^c UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Amino acids; Betaines; Biosynthesis ergothioneine; Hypaphorine; Methyltransferases

Indexed keywords

AROMATIC AMINO ACID; BETAINE; HISTIDINE DERIVATIVE; METHYLTRANSFERASE; METHYLTRANSFERASE EGTD; N ALPHA DIMETHYLHISTIDINE; S ADENOSYLMETHIONINE; THIONEINE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG; FUNGAL PROTEIN; HISTIDINE; RECOMBINANT PROTEIN; S ADENOSYLHOMOCYSTEINE;

AMINO ACID SYNTHESIS; ARTICLE; ASCOMYCETES; BASIDIOMYCETES; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME SPECIFICITY; FUNGAL GENE; HYDROPHILICITY; METHYLATION; MOLECULAR INTERACTION; NONHUMAN; AMINO ACID SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; METABOLISM; MOLECULAR GENETICS; MUTATION; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; X RAY CRYSTALLOGRAPHY;

BACTERIA (MICROORGANISMS); FUNGI;

AMINO ACID SEQUENCE; ASCOMYCOTA; BASIDIOMYCOTA; BETAINE; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; ERGOTHIONEINE; ESCHERICHIA COLI; FUNGAL PROTEINS; GENE EXPRESSION; HISTIDINE; METHYLTRANSFERASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTATION; RECOMBINANT PROTEINS; S-ADENOSYLHOMOCYSTEINE; S-ADENOSYLMETHIONINE; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY; TRYPTOPHAN;

EID: 84919752708     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201402522     Document Type: Article

References (43)

1. a) D. B. Melville, M. L. Ludwig, E. Inamine, J. R. Rachele, J. Biol. Chem. 1959, 234, 1195-1198
2. b) F. P. Seebeck, J. Am. Chem. Soc. 2010, 132, 6632-6633
3. c) M. H. Bello, V. Barrera-Perez, D. Morin, L. Epstein, Fungal Genet. Biol. 2012, 49, 160-172
4. d) C. Pfeiffer, B. Surek, E. Schöming, D. Gründemann, Food Chem. 2011, 129, 1766-1769
5. e) C. Tanret, C. R. Acad. Sci. 1909, 149, 222-224
6. f) D. Gründemann, Prev. Med. 2012, 54, S71-S74
7. g) I. K. Cheah, B. Halliwell, Biochim. Biophys. Acta 2012, 1822, 784-793
8. h) R. C. Fahey, Biochim. Biophys. Acta 2013, 1830, 3182-3198.
9. a) I. K. Cheah, R. L. Ong, J. Gruber, T. S. Yew, L. F. Ng, C. B. Chen, B. Halliwell, Free Radical Res. 2013, 47, 1036-1045
10. b) B. D. Paul, S. H. Snyder, Cell Death Differ. 2009, 16, S149-S149
11. c) C. Sao Emani, M. J. Williams, I. J. Wiid, N. F. Hiten, A. J. Viljoen, R.-D. D. Pietersen, P. D. van Helden, B. Baker, Antimicrob. Agents Chemother. 2013, 57, 3202-3207.
12. a) T. H. Chen, N. Murata, Plant Cell Environ. 2011, 34, 1-20
13. b) S. G. Lee, Y Kim, T. D. Alpert, A. Nagata, J. M. Jez, J. Biol. Chem. 2012, 287, 1426-1434.
14. a) A. Tsopmo, A.D. Muir, J. Agric. Food Chem. 2010, 58, 8715-8721
15. b) B. O. Keller, B. T. Wu, S. S. Li, V. Monga, S. M. Innis, J. Agric. Food Chem. 2013, 61, 7654-7660.
16. T. Kawano, Plant Cell Rep. 2003, 21, 829-837.
17. a) T. Bernard, G. Goas, J. Hamelin, M. Joucla, Phytochemistry 1981, 20, 2325-2326
18. b) T. Bernard, M. Joucla, G. Goas, J. Hamelin, Phytochemistry 1980, 19, 1967-1969
19. c) A. Mollica, M. Locatelli, A. Stefanucci, F. Pinnen, Molecules 2012, 17, 6083-6099.
20. K. M. Dorgan, W. L. Wooderchak, D. P. Wynn, E. L. Karschner, J. F. Alfaro, Y. Q. Cui, Z. S. Zhou, J. M. Hevel, Anal. Biochem. 2006, 350, 249-255.
21. R. Gana, S. Rao, H. Huang, C. Wu, S. Vasudevan, BMC Struct. Biol. 2013, 13, 6.
22. a) S. Horowitz, L. M. A. Dirk, J. D. Yesselman, J. S. Nimtz, U. Adhikari, R. A. Mehl, S. Schreiner, R. L. Houtz, H. M. Al-Hashimi, R. C. Trievel, J. Am. Chem. Soc. 2013, 135, 15536-15548
23. b) S. Horowitz, R. C. Trievel, J. Biol. Chem. 2012, 287, 41576-41582.
24. R. D. Finn, A. M. Bateman, J. Clements, P. Coggill, R. Y. Eberhardt, S. R. Eddy, A. Heder, K. Hetherington, J. Mistry, E. L. Sonnhammer, J. Tate, M. Punta, Nucleic Acids Res. 2014, 42, D222-D230.
25. G. W. Jones, S. Doyle, D. A. Fitzpatrick, Gene 2014, 549, 161-170.
26. C. A. Carollo, A. L. Calil, L. A. Schiave, T. Guaratini, D. W. Roberts, N. P. Lopes, G. U. Braga, Fungal Genet. Biol. 2010, 114, 473-480.
27. C. J. Gagliardi, R. A. Binstead, H. H. Thorp, T. J. Meyer, J. Am. Chem. Soc. 2011, 133, 19594-19597.
28. a) M. D. Toscano, K. J. Woycechowsky, D. Hilvert, Angew. Chem. Int. Ed. 2007, 46, 3212-3236
29. Angew. Chem. 2007, 119, 3274-3300
30. b) H. W. Wilks, K. W. Hart, R. Feeney, C. R. Dunn, H. Muirhead, W. N. Chia, D. A. Barstow, T. Atkinson, A. R. Clarke, J. J. Holbrook, Science 1988, 242, 1541-1544.
31. A. Vit, L. E. Misson, W. Blankenfeldt, F. P. Seebeck, Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 2014, 70, 676-680.
32. C. Vonrhein, E. Blanc, P. Roversi, G. Bricogne, Methods Mol. Biol. 2007, 364, 215-230.
33. G. Langer, S. X. Cohen, V. S. Lamzin, A. Perrakis, Nat. Protoc. 2008, 3, 1171-1179.
34. W. Kabsch, Acta Crystallogr. Sect. D Biol. Crystallogr. 2010, 66, 125-132.
35. a) P. R. Evans, Acta Crystallogr. Sect. D Biol. Crystallogr. 2011, 67, 282-292
36. b) G. N. Murshudov, P. Skubak, A.A. Lebedev, N.S. Pannu, R. A. Steiner, R. A. Nicholls, M. D. Winn, F. Long, A. A. Vagin, Acta Crystallogr. Sect. D Biol. Crystallogr. 2011, 67, 355-367.
37. A. Vagin, A. Teplyakov, J. Appl. Crystallogr. 1997, 30, 1022-1025.
38. A. W. Schüttelkopf, D. M. F. van Aalten, Acta Crystallogr. Sect. D Biol. Crystallogr. 2004, 60, 1355-1363.
39. N. W. Moriarty, R. W. Grosse-Kunstleve, P. D. Adams, Acta Crystallogr. Sect. D Biol. Crystallogr. 2009, 65, 1074-1080.
40. P. D. Adams, P. V Afonie, G. Bunkoczi, V B. Chen, I. W. Davies, N. Echols, J. J. Headd, L. W. Hung, G.J. Kapral, R. W. Grosse-Kunstleve, A. J. McCoy, N.W. Moriarty, R. Oeffner, R. J. Read, D.C. Richardson, J.S. Richardson, T. C. Terwillinger, P. H. Zwart, Acta Crystallogr. Sect. D Biol. Crystallogr. 2010, 66, 213-221.
41. V B. Chen, W. B. Arendall, J.J. Headd, D. A. Keedy, R. M. Immormino, G.J. Kapral, L. W. Murray, J. S. Richardson, D. C. Richardson, Acta Crystallogr. Sect. D Biol. Crystallogr. 2010, 66, 12-21.
42. W. L. DeLano, The PyMol User's Manual, DeLano Scientific, San Carlos, CA, USA; 2002, 2002.
43. H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucleic Acids Res. 2000, 28, 235-242.