Structure of ACC synthase inactivated by the mechanism-based inhibitor L-vinylglycine

FEBS Letters

Volumn 579, Issue 11, 2005, Pages 2458-2462

  Capitani, Guido ^a   Tschopp, Markus ^a   Eliot, Andrew C ^b,c   Kirsch, Jack F ^b   Grütter, Markus G ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

ACC synthase; Ethylene biosynthesis; Mechanism based inhibitor; Pyridoxal 5 phosphate; Substrate

Indexed keywords

1 AMINOCYCLOPROPANECARBOXYLATE SYNTHASE; 2 OXOBUTYRIC ACID; AMMONIA; CARBON; ENZYME; ENZYME INHIBITOR; GAMMA CARBON; GLYCINE DERIVATIVE; IMINE; LYSINE; PHOSPHATE; UNCLASSIFIED DRUG; VINYLGLYCINE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; COVALENT BOND; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME INACTIVATION; ENZYME STRUCTURE; ENZYME SUBSTRATE; MICHAEL ADDITION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 17644394581     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2005.03.048     Document Type: Article

References (28)

1. S.F. Yang, and N.E. Hoffmann Ethylene biosynthesis and its regulation in higher plants Annu. Rev. Plant. Physiol. 35 1984 155 189
2. F.B. Abeles, P.W. Morgan, and M.E. Saltweit Jr. Ethylene in plant biology 1992 Academic Press San Diego, CA
3. G. Capitani, E. Hohenester, L. Feng, P. Storici, J.F. Kirsch, and J.N. Jansonius Structure of 1-aminocyclopropane-1-carboxylate synthase, a key enzyme in the biosynthesis of the plant hormone ethylene J. Mol. Biol. 294 1999 745 756
4. G. Capitani, D.L. McCarthy, H. Gut, M.G. Grutter, and J.F. Kirsch Apple 1-aminocyclopropane-1-carboxylate synthase in complex with the inhibitor l-aminoethoxyvinylglycine. Evidence for a ketimine intermediate J. Biol. Chem. 277 2002 49735 49742
5. G. Capitani, A.C. Eliot, H. Gut, R.M. Khomutov, J.F. Kirsch, and M.G. Grutter Structure of 1-aminocyclopropane-1-carboxylate synthase in complex with an amino-oxy analogue of the substrate: implications for substrate binding Biochim. Biophys. Acta 1647 2003 55 60
6. Q. Huai, Y. Xia, Y. Chen, B. Callahan, N. Li, and H. Ke Crystal structures of 1-aminocyclopropane-1-carboxylate (ACC) synthase in complex with aminoethoxyvinylglycine and pyridoxal-5′-phosphate provide new insight into catalytic mechanisms J. Biol. Chem. 276 2001 38210 38216
7. D.L. McCarthy, G. Capitani, L. Feng, M.G. Gruetter, and J.F. Kirsch Glutamate 47 in 1-aminocyclopropane-1-carboxylate synthase is a major specificity determinant Biochemistry 40 2001 12276 12284
8. L. Feng, and J.F. Kirsch l-Vinylglycine is an alternative substrate as well as a mechanism-based inhibitor of 1-aminocyclopropane-1-carboxylate synthase Biochemistry 39 2000 2436 2444
9. W.K. Yip, J.G. Dong, J.W. Kenny, G.A. Thompson, and S.F. Yang Characterization and sequencing of the active site of 1-aminocyclopropane-1- carboxylate synthase Proc. Natl. Acad. Sci. USA 87 1990 7930 7934
10. S. Satoh, and S.F. Yang Specificity of S-adenosyl-l-methionine in the inactivation and the labeling of 1-aminocyclopropane-1-carboxylate synthase isolated from tomato fruits Arch. Biochem. Biophys. 271 1989 107 112
11. M.F. White, J. Vasquez, S.F. Yang, and J.F. Kirsch Expression of apple 1-aminocyclopropane-1-carboxylate synthase in Escherichia coli: kinetic characterization of wild-type and active-site mutant forms Proc. Natl. Acad. Sci. USA 91 1994 12428 12432
12. Z. Otwinowski, and W. Minor Processing of X-ray diffraction data collected in oscillation mode C.W. Carter Jr. R.M. Sweet Meth. Enzymol. vol. 276 1997 Academic Press New York, NY 307 326
13. Collaborative computational project number 4 (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr. D 50, 760-763
14. A.T. Brunger Crystallography & NMR system: a new software suite for macromolecular structure determination Acta Crystallogr. D 54 1998 905 921
15. T.A. Jones, and M. Kjeldgaard O - The Manual, vers. 5.10.3 1991 Uppsala University Uppsala, Sweden
16. R.A. Laskowski, M.W. MacArthur, D.S. Moss, and J.M. Thornton PROCHECK: a program to check the stereochemical quality of protein structures J. Appl. Crystallogr. 26 1993 283 291
17. R.W. Hooft, G. Vriend, C. Sander, and E.E. Abola Errors in protein structures Nature 381 1997 272
18. G. Dardenne, J. Casimir, M. Marlier, and P.O. Larsen 2(R)-amino-3- butenoic(vinylglycine) acid in Carpophores of Rhodophyllus-Nidorosus Phytochemistry 13 1974 1897 1900
19. P. Friis, P. Helboe, and P.O. Larsen Synthesis and resolution of vinylglycine, a beta,gamma-unsaturated alpha-amino-acid Acta Chem. Scand. Ser. B - Org. Chem. Biochem. B 28 1974 317 321
20. H. Gehring, R.R. Rando, and P. Christen Active-site labeling of aspartate aminotransferases by the beta,gamma-unsaturated amino acid vinylglycine Biochemistry 16 1977 4832 4836
21. Y. Asada, K. Tanizawa, K. Yonaha, and K. Soda Deamination and gamma-addition reactions of vinylglycine catalyzed by yeast kynurenine aminotransferase, and suicidal inactivation of the enzyme during its processing Agric. Biol. Chem. 52 1988 2873 2878
22. A.C. Eliot, and J.F. Kirsch Avoiding the road less traveled: how the topology of enzyme-substrate complexes can dictate product selection Acc. Chem. Res. 36 2003 757 765
23. R.R. Rando Irreversible inhibition of aspartate aminotransferase by 2-amino-3-butenoic acid Biochemistry 13 1974 3859 3863
24. W.P. Burmeister Structural changes in a cryo-cooled protein crystal owing to radiation damage Acta Crystallogr. D 56 2000 328 341
25. S. Satoh, and Y. Esashi Inactivation of 1-aminocyclopropane-1-carboxylic acid synthase of etiolated mung bean hypocotyl segments by its substrate, S-adenosyl-l-methionine Plant Cell Physiol. 27 1986 285 291
26. S. Ko, A.C. Eliot, and J.F. Kirsch S-methylmethionine is both a substrate and an inactivator of 1-aminocyclopropane-1-carboxylate synthase Arch. Biochem. Biophys. 421 2004 85 90
27. F. Bourgis S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase Plant Cell 11 1999 1485 1497
28. H. Yoshii, and H. Imaseki Regulation of auxin-induced ethylene biosynthesis - repression of inductive formation of 1-aminocyclopropane-1- carboxylate synthase by ethylene Plant Cell Physiol. 23 1982 639 649