Ethylene biosynthesis: Processing of a substrate analog supports a radical mechanism for the ethylene-forming enzyme

Chemistry and Biology

Volumn 5, Issue 1, 1998, Pages 49-57

  Pirrung, Michael C ^a   Cao, Jun ^a   Chen, Jrlung ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

1 aminocyclobutanecarboxylate; Biosynthesis; Ethylene; Hydroxylation; Radical

Indexed keywords

EID: 0031906392     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90086-2     Document Type: Article

References (48)

1. Kende, H. (1993). Ethylene biosynthesis. Annu. Rev. Plant Physiol. Plant Mol. Biol. 44, 283-307.
2. Pirrung, M.C. (1994). Ethylene biosynthesis from 1-aminocyclopropanecarboxylic acid: interplay of molecular genetics and organic mechanism. In Natural and Engineered Pest Management Agents, ACS Symp. Ser. 551, (Hedin, P.A., Menn, J.J. & Hollingworth, R.M., eds), pp. 436-448, American Chemical Society, Washington, DC.
3. Pirrung, M.C., Kaiser, L.M. & Chen, J. (1993). Purification and properties of the apple fruit ethylene-forming enzyme. Biochemistry 32, 7445-7450.
4. Dilley, D.R., et al., & Bowers, A. (1993). Purification and characterization of ACC oxidase and its expression during ripening in apple fruit. Curr. Plant Sci. Biotechnol. Agric. 16, 46-52.
5. Dong, J.G., Fernandez-Maculet, J.C. & Yang, S.F. (1992). Purification and characterization of 1-aminocyclopropane-1-carboxylate oxidase from apple fruit. Proc. Natl Acad. Sci. USA 89, 9789-9793.
6. Dupille E., et al., & Pech, J.-C. (1992). Stabilisation in vitro et purification de l'enzyme formant l'ethylene chez la pomme. C. R. Acad. Sci., Paris, ser. III (2), 77-84.
7. Pirrung, M.C., Cao, J. & Chen, C, (1995). Ethylene biosynthesis. 12. Analog approac̈h to the active site topography of the ethylene-forming enzyme. Novel hydroxamate inhibitors. J. Org. Chem. 60, 5790-5794.
8. Escribano, M.I., Merodio, C. & John, P. (1996). Characterization of 1-aminocyclopropane-1-carboxylate oxidase partially purified from cherimoya fruit. J. Agric. Food Chem. 44, 730-735.
9. Moya-Leon, MA & John, P. (1995). Characterization of 1-aminocyclopropane-1-carboxylate oxidase from banana fruit. Phytochemistry 39, 15-20.
10. Wilson, I.D., Zhu, Y., Burmeister, D.M. & Dilley, D.R. (1993). Apple ripening related cDNA clone pAP4 confers ethylene-forming ability in transformed Saccharomyces cerevisiae. Plant Physiol. 102, 783-788.
11. Dilley, D.R. & Zhu, Y. (1994). Purification and characterization of genetic engineered 1-aminocyclopropane-1-carboxylate oxidase overexpressed in E. coli [Abstract 125]. Plant Physiol. Suppl., 33.
12. Zhang, Z., Schofield, C.J., Baldwin, J.E., Thomas, P. & John, P. (1995). Expression, purification and characterization of 1-aminocyclopropane-1-carboxylate oxidase from tomato in Escherichia coli. Biochem. J. 307, 77-85.
13. Gibson, E.J., Zhang, Z., Baldwin, J.E. & Schofield, C.J. (1997). Substrate analogue and inhibition studies on ACC oxidase: D- but not L-valine is a substrate yielding iso-butanal. Phytochemistry, in press.
14. Itturriagagoita-Bueno, T., Gibson, E.J., Schofield, C.J. & John, P. (1996). Inhibition of 1-aminocyclopropane-1-carboxylate oxidase by 2-oxoacids. Phytochemistry 43, 343-349.
15. Smith, J.J., Zhang, Z.H., Schofield, C.J., John, P., Baldwin, J.E. (1994). Inactivation of 1-aminocyclopropane-1-carboxylate oxidase. J. Exp. Bot. 45, 521-527.
16. Baldwin, J.E., Adlington, R.M. & Rawlings, B.J. (1985). A convenient synthesis of regiospecifically 2-alkylated-3-deuteriated-1-aminocyclopropyl-1-carboxylic acids. Tetrahedron Lett. 26, 481-484.
17. Pirrung, M.C., Dunlap, S.E. & Trinks, U.P. (1989). Ethylene biosynthesis. 10. Synthesis and study of racemic, (1R,2S)-, and (1 S,2R)-1-amino-2-hydroxymethyl-cyclopropanecarboxylic acid. Helv. Chim. Acta. 72, 1301-1310.
18. Pirrung, M.C. & McGeehan, G.M. (1986). Ethylene biosynthesis. 6. Methylaminocyclopropanecarboxylic acid. J. Org. Chem. 51, 2103-2106.
19. Liu, Y., Su. L.-Y. & Yang, S.F. (1984). Metabolism of alphaaminoisobutyric acid in mung bean hypocotyls in relation to metabolism of 1-aminocyclopropyl-1-carboxylic acid. Planta 161, 439-443.
20. Pirrung, M.C. (1983). Ethylene biosynthesis 2. Stereochemistry of ripening, stress, and model reactions. J. Am. Chem. Soc. 105, 7207-7209.
21. Macdonald, T., Zirvi, K., Burka, L., Peyman, P. & Guengerich, F.P. (1982). Mechanism of cytochrome P-450 inhibition by cyclopropylamines. J. Am. Chem. Soc. 104, 2050-2052.
22. Tullman, R.H. & Hanzlik, R.P. (1984). Inactivation of cytochrome P-450 and monoamine oxidase by cyclopropylamines. Drug Metab. Rev. 15, 1163-1182.
23. Horner, J.H., Martinez, F.N., Musa, O.M., Newcomb, M. & Shahin, H.E. (1995). Kinetics of dialkylaminium cation radical reactions: radical clocks, solvent effects, acidity constants, and rate constants for reactions with hydrogen atom donors. J. Am. Chem. Soc. 117, 11124-11133.
24. Qin, X.-Z. & Williams, F. (1987). ESR studies of the radical cation mechanism of the ring opening of cyclopropylamines. J. Am. Chem. Soc. 109, 595-596.
25. Pirrung, M.C. & McGeehan, G.M. (1986). Ethylene biosynthesis. 7. Secondary isotope effects. J. Am. Chem. Soc. 108, 5647-5648.
26. Pirrung, M.C. (1987). Ethylene biosynthesis. 8. Structural and theoretical studies. J. Org. Chem. 52, 4179-4185.
27. Pirrung, M.C. & McGeehan, G.M. (1985). Cyclopropyl-ACC. An investigation of the mechanism of ethylene biosynthesis. Angew. Chem. Int. Ed. Engl. 24, 1044-1045.
28. Musa, O.M., Horner, J.H., Shahin, H.E. & Newcomb, M. (1996). A kinetic scale for dialkylaminyl radical reactions. J. Am. Chem. Soc. 118, 3862-3868.
29. Yang, S.F. (1989). Metabolism of 1-aminocyclopropane-1-carboxylic acid in relation to ethylene biosynthesis Rec. Adv. Phytochem. 23, 263-287.
30. Newcomb, M., Le Tadic-Biadatti, M.-H., Chestney, D.L, Roberts, E.S. & Hollenberg, P.F. (1995). A nonsynchronous concerted mechanism for cytochrome P-450 catalyzed hydroxylation. J. Am. Chem. Soc. 117, 12085-12091.
31. Yelekci, K., Lu, X. & Silverman, R.B. (1989). Electron spin resonance studies of monoamine oxidase b. First direct evidence for a substrate radical intermediate J. Am. Chem. Soc. 111, 1138-1140.
32. Swarts, F. (1927). Trifluoroacetoacetic acid and ester, trifluorodimethylketone. Bull. Sci. Acad. Roy. Belg. 13, 175; [Chem. Abstr. (1928). 22, 58.].
33. Swarts, F. (1927). Trifluoroacetoacetic acid and ester, trifluorodimethylketone. Bull. Sci. Acad. Roy. Belg. 13, 175; [Chem. Abstr. (1928). 22, 58.].
34. Lizada, M.C. & Yang, S.F. (1979). A simple and sensitive assay for 1-aminocyclopropane-1-carboxylic acid. Anal. Biochem. 100, 140-145.
35. Adlington, R.M., Baldwin, J.E. & Rawlings, B.J. (1983). On the stereochemistry of ethylene biosynthesis J. Chem. Soc. Chem. Commun., 290-291.
36. Pirrung, M.C. & McGeehan, G.M. (1983). Ethylene biosynthesis. 1. A model for two reactive intermediates. J. Org. Chem. 48, 5143-5144.
37. Baldwin, J.E., Jackson, D.A., Adlington, R.M. & Rawlings, B.J. (1985). The sterochemistry of oxidation of 1-aminocyclopropane-1-carboxylic acid. J. Chem. Soc. Chem. Commun., 206-207.
38. Salmon, J.A., Jackson, W.P. & Garland, L.G. (1991). Inhibition of 5-lipoxygenase: development of hydroxamic acids and hydroxyureas as potential therapeutic agents. Adv. Prostaglandin Thromboxane Leukot. Res. 21 A, 109-112.
39. Baldwin, J.E., Adlington, R.M, Kang, T.W., Lee, E. & Schofield, C.J. (1987). Ring expansion of penams to cephams: a possible biomimetic process. J. Chem. Soc. Chem. Commun., 104-106.
40. Ullrich, V. & Brugger, R. (1994). Prostacyclin and thromboxane synthase: new aspects of hemethiolate catalysis. Angew. Chem, Int. Ed. Engl. 33, 1911-1919.
41. Siegel, B. (1979), α-Ketoglutarate dependent dioxygenases: a mechanism for prolyl hydroxylase action. Bioorg. Chem. 8, 219-226.
42. Nambiar, K.P., Stauffer, D.M., Kolodziej, P.A. & Benner, S.A. (1983). A mechanistic basis for the stereoselectivity of enzymic transfer of hydrogen from nicotinamide cofactors. J. Am. Chem. Soc. 105, 5886-5890.
43. Stackhouse, J., Nambiar, K.P., Burbaum, J.J., Stauffer, D.M. & Benner, S.A. (1985). Dynamic transduction of energy and internal equilibria in enzymes. A reexamination of pyruvate kinase. J. Am. Chem. Soc. 107, 2757-2763.
44. Salowe, S.P., Marsh, E.N. & Townsend, C.A. (1990). Purification and characterization of clavaminate synthase from Streptomyces clavuligerus: an unusual oxidative enzyme in natural products biosynthesis. Biochemistry 29, 6499-6508.
45. Woodson, W.R., Park, K.Y., Drory, A., Larsen, P.B, & Wang, H. (1992). Expression of ethylene biosynthetic pathway transcripts in senescing carnation flowers. Plant Physiol. 99, 526-532.
46. Pirrung, M.C. & Trinks, U.P. (1989). Ethylene biosynthesis. 9. Aminocyclopropenecarboxylic acid. J. Chem. Soc. Chem. Commun., 857-859.
47. Marchand-Brynaert, J., Bounkhala-Khrouz, Z., Vanlierde, H. & Ghosez, L. (1990). Oxaziridines and nitrones as potential inhibitors of bacterial D,D-peptidases. Heterocycles 30, 971-982.
48. Sissons, C.H. (1976). Improved technique for accurate and convenient assay of biological reactions liberating carbon-14 dioxide. Anal. Biochem. 70, 454-462.