Abstract
The characteristics of the conversion of 1-aminocyclopropane-1-carboxylic acid (ACC) to ethylene by pea (Pisum sativum L.) epicotyls and by pea epicotyl enzyme are compared. Of the four stereoisomers of 1-amino-2-ethylcyclopropane-1-carboxylic acid (AEC), only (1R,2S)-AEC is preferentially converted to 1-butene in pea epicotyls. This conversion is inhibited by ACC, indicating that butene production from (1R,2S)-AEC and ethylene production from ACC are catalyzed by the same enzyme. Furthermore, pea epicotyls efficiently convert ACC to ethylene with a low K m (66 μM) for ACC and do not convert 4-methylthio-2-oxo-butanoic acid (KMB) to ethylene, thus demonstrating high specificity for its substrate. In contrast, the reported pea epicotyl enzyme which catalyzes the conversion of ACC to ethylene had a high K m (389 mM) for ACC and readily converted KMB to ethylene. We show, moreover, that the pea enzyme catalyzes the conversion of AEC isomers to butene without stereodiscrimination. Because of its lack of stereospecificity, its low affinity for ACC and its utilization of KMB as a substrate, we conclude that the reported pea enzyme system is not related to the in-vivo ethylene-forming enzyme.
Similar content being viewed by others
Abbreviations
- ACC:
-
1-Amino cyclopropane-1-carboxylic acid
- AEC:
-
1-amino-2-ethylcyclopropane-1-carboxylic acid
- EFE:
-
ethylene-forming enzyme
- KMB:
-
4-methylthio-2-oxobutanoic acid
References
Adams, D.O., Yang, S.F. (1979) Ethylene biosynthesis: identification of 1-aminocyclopropane-1-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc. Natl. Acad. Sci. USA 76, 170–174
Apelbaum, A., Burgoon, A.C., Anderson, J.D., Solomos, T., Lieberman, M. (1981) Some characteristics of the system converting 1-aminocyclopropane-1-carboxylic acid to ethylene. Plant Physiol. 67, 80–84
Boller, T., Herner, R.C., Kende, H. (1979) Assay for and enzymatic formation of an ethylene precursor, 1-aminocyclopropane-1-carboxylic acid. Planta 145, 293–303
Diguiseppi, J., Fridovich, I. (1980) Ethylene from 2-keto-4-thiomethylbutyric acid: the Haber-Weiss reaction. Arch. Biochem. Biophys. 205, 323–329
Hoffman, N.E., Yang, S.F., Ichihara, A., Sakamura, S. (1982) Stereospecific conversion of 1-aminocyclopropanecarboxylic acid to ethylene by plant tissues. Conversion of stereoisomers of 1-amino-2-ethylcyclopropanecarboxylic acid to 1-butene. Plant Physiol. 70, 195–199
Ichihara, A., Shiraishi, K., Sakamura, S. (1977) Partial synthesis and stereochemistry of coronatine. Tetrahedron Lett. 269–272
Konze, J.R., Kende, H. (1979) Ethylene formation from 1-aminocyclopropane-1-carboxylic acid in homogenates of etiolated pea seedlings. Planta 146, 293–301
Legge, R.L., Thompson, J.E., Baker, J.E. (1982) Free radicalmediated formation of ethylene from 1-aminocyclopropane-1-carboxylic acid: a spin-trap study. Plant Cell Physiol. 23, 171–177
Lizada, M.C.C., Yang, S.F. (1979) A simple and sensitive assay for 1-aminocyclopropane-1-carboxylic acid. Anal. Biochem. 100, 140–145
Lürssen, K., Naumann, K., Schröder, R. (1979) 1-Aminocyclopropane-1-carboxylic acid—an intermediate of ethylene biosynthesis in higher plants. Z. Pflanzenphysiol. 92, 285–294
Machackova, I., Zmrhal, Z. (1981) Is peroxidase involved in ethylene biosynthesis? Physiol. Plant. 53, 479–482
Mattoo, A.K., Achilea, O., Fuchs, Y., Chalutz, E. (1982) Membrane association and some characteristics of the ethylene forming enzyme from etiolated pea seedling. Biochem. Biophys. Res. Commun. 105, 271–278
Mayak, S., Legge, R.L., Thompson, J.E. (1981) Ethylene formation from 1-aminocyclopropane-1-carboxylic acid by microsomal membranes from senescing carnation flowers. Planta 153, 49–55
McKeon, T.A., Hoffman, N.E., Yang, S.F. (1982) The effect of plant-hormone pretreatments on ethylene production and synthesis of 1-aminocyclopropane-1-carboxylic acid in water-stressed wheat leaves. Planta 155, 437–443
McRae, D.G., Baker, J.E., Thompson, J.E. (1982) Evidence for involvement of the superoxide radical in the conversion of 1-aminocyclopropane-1-carboxylic acid to ethylene by pea microsomal membranes. Plant Cell Physiol. 23, 375–383
Rohwer, F., Mader, M. (1981) The role of peroxidase in ethylene formation from 1-aminocyclopropane-1-carboxylic acid. Z. Pflanzenphysiol. 104, 363–372
Rohwer, F., Schierle, J. (1982) Effect of light on ethylene production: red light enhancement of 1-aminocyclopropane-1-carboxylic acid concentration in etiolated pea shoots. Z. Pflanzenphysiol. 107, 295–300
Shiraishi, K., Ichihara, A., Sakamura, S. (1977) Facile stereoselective synthesis of (+)- and (-)-allocoronamic acids. Agric. Biol. Chem. 41, 2497–2498
Vioque, A., Albi, M.A., Vioque, B. (1981) Role of IAA-oxidase in the formation of ethylene from 1-aminocyclopropane-1-carboxylic acid. Phytochemistry 20, 1473–1475
Yang, S.F. (1969) Further studies on ethylene formation from α-keto-γ-methylthiobutyric acid or β-methylthiopropionaldehyde by peroxidase in the presence of sulfite and oxygen. J. Biol. Chem. 244, 4360–4365
Yang, S.F. (1980) Regulation of ethylene biosynthesis. Hort-Science 15, 238–243
Yemm, E.W., Cocking, E.C. (1955) The determination of amino-acids with ninhydrin. Analyst 80, 209–213
Yu, Y.B., Yang, S.F. (1979) Auxin-induced ethylene production and its inhibition by aminoethoxyvinylglycine and cobalt ion. Plant Physiol. 64, 1074–1077
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
McKeon, T.A., Shang Fa Yang A comparison of the conversion of 1-amino-2-ethylcyclopropane-1-carboxylic acid stereoisomers to 1-butene by pea epicotyls and by a cell-free system. Planta 160, 84–87 (1984). https://doi.org/10.1007/BF00392470
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00392470