Kinetic analysis of the inhibition of phenylalanine ammonia-lyase by 2-aminoindan-2-phosphonic acid and other phenylalanine analogues

Phytochemistry

Volumn 62, Issue 3, 2003, Pages 415-422

  Appert, Christoph ^a   Zoń, Jerzy ^b   Amrhein, Nikolaus ^a  

^a ETH ZURICH   (Switzerland)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

2 Aminoindan 2 phosphonic acid (AIP); Petroselinum crispum; Phenylalanine ammonia lyase (PAL); Slow binding enzyme inhibitor

Indexed keywords

2 AMINOINDAN 2 PHOSPHONIC ACID; CARBOXYLIC ACID DERIVATIVE; ENZYME INHIBITOR; INDENE DERIVATIVE; ISOENZYME; PHENYLALANINE AMMONIA LYASE; PHENYLALANINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME KINETICS; EQUILIBRIUM CONSTANT; NONHUMAN; PARSLEY; PROTEIN EXPRESSION; TIME;

BINDING SITES; BINDING, COMPETITIVE; ENZYME INHIBITORS; ISOENZYMES; KINETICS; PETROSELINUM; PHENYLALANINE; PHENYLALANINE AMMONIA-LYASE; PHOSPHONIC ACIDS;

PETROSELINUM CRISPUM;

EID: 12244298867     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00561-7     Document Type: Article

References (29)

1. Amrhein, N., Gödeke, K.-H., Kefeli, V.I., 1976. The estimation of relative intracellular phenylalanine ammonia-lyase (PAL)-activities and the modulation in vivo and in vitro by competitive inhibitors. Ber. Deutsch. Bot. Ges. 89, 247-259.
2. Amrhein, N., Gödeke, K.H., 1977. α-Aminooxy-β-phenylpropionic acid- a potent inhibitor of phenylalanine ammonia-lyase in vitro and in vivo. Plant Sci. Lett. 8, 313-317.
3. Amrhein, N., Holländer, H., 1979. Inhibition of anthocyanin formation in seedlings and flowers by the enantiomers of α-aminooxy-βphenylpropionic acid and their N-benzyloxycarbonyl derivatives. Planta 144, 385-389.
4. Amrhein, N., 1986. Specific inhibitors as probes into the biosynthesis and metabolism of aromatic amino acids. In: Conn, E.E. (Ed.), The Shikimic Acid Pathway. Rec. Adv. Phytochem., Vol. 20. Plenum Press, New York, London, pp. 83-117.
5. Appert, C., Logemann, E., Hahlbrock, K., Schmid, J., Amrhein, N., 1994. Structural and catalytic properties of the four phenylalanine ammonia-lyases from parsley (Petroselinum crispum Nym.). Eur. J. Biochem. 225, 491-499.
6. Cha, S., 1975. Tight-binding inhibitors-I. Kinetic behavior. Biochem. Pharmacol. 24, 2177-2185.
7. Cha, S., 1976a. Erratum to "Cha, S., 1975. Tight-binding inhibitors-I. Kinetic behavior. Biochem. Pharmacol. 24, 2177-2185". Biochem. Pharmacol. 25, 1561.
8. Cha, S., 1976b. Tight-binding inhibitors III. A new approach for the determination of competition between tight-binding inhibitors and substrates - inhibition of adenosine deaminase by coformycin. Biochem. Pharmacol. 25, 2695-2702.
9. De-Eknamkul, W., Ellis, B.E., 1987. Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis. Phytochemistry 26, 1941-1946.
10. Hanson, K.R., Havir, E.A., 1981. Phenylalanine ammonia-lyase. In: Stumpf, P.K., Conn, E.E. (Eds.), The Biochemistry of Plants, Vol. 7. Academic Press, New York, pp. 577-625.
11. Hanson, K.R., 1981. Phenylalanine ammonia-lyase: mirror-image packing of D- and L- phenylalanine and D- and L-transition state analogs into the active site. Arch. Biochem. Biophys. 211, 575-588.
12. Henderson, P.J.F., 1972. A linear equation that describes the steadystate kinetics of enzymes and subcellular particles interacting with tightly bound inhibitors. Biochem. J. 127, 321-333.
13. Hollander, H., Kiltz, H.-H., Amrhein, N., 1979. Interference of L-α-aminooxy-β-phenylpropionic acid with phenylalanine metabolism in buckwheat. Z. Naturforsch. 34C, 1162-1173.
14. Janas, K.M., Filipiak, A., Kowalik, J., Mastalerz, P., Knypl, J.S., 1985. 1-Amino-2-phenylphosphonic acid: an inhibitor of Lphenylalanine ammonia-layse in vitro. Acta Biochem. Polon. 32, 131-143.
15. Laber, B., Kiltz, H.-H., Amrhein, N., 1986. Inhibition of phenylalanine ammonia-lyase in vitro and in vivo by (1-amino-2-phenylethyl) phosphoric acid, the phosphonic analogue of phenylalanine. Z. Naturforsch. 41C, 33-39.
16. Liebermann, C., Zsuffa, M., 1911. Zur Carboxylierung mehrkerniger aromatischer Kohlenwasserstoffe. Chem. Ber. 44, 202-210.
17. Morrison, J.F., 1982. The slow-binding and slow, tight-binding inhibition of enzyme-catalysed reactions. Trends Biochem. Sci. 7., 102-105.
18. Morrison, J.F., Walsh, C.T., 1987. The behavior and the significance of slow-binding enzyme inhibitors. Adv. Enzymol. Relat. Areas. Mol. Biol. 61, 201-368.
19. Rösler, J., Krekel, F., Amrhein, N., Schmid, J., 1997. Maize phenylalanine ammonia-lyase has tyrosine ammonia-lyase activity. Plant Physiol. 113, 175-179.
20. Röther, D., Merkel, D., Rétey, J., 2000. Spectroscopic evidence for a 4-methylidene imidazol-5-one in histidine ans phenylalanine ammonia-lyases. Angew. Chem. Int. Eds. 39, 2462-2464.
21. Röther, D., Poppe, L., Morlock, G., Viergutz, S., Rétey, J., 2002. An active site homology model of phenylalanine ammonia-lyase from Petroselinum crispum. Eur. J. Biochem. 269, 3065-3075.
22. Schloss. J.V., 1988. Significance of slow-binding enzyme inhibition and its relationship to reaction-intermediate analogues. Acc. Chem. Res. 21, 348-353.
23. Schloss, J.V., 1989. Modern aspects of enzyme inhibition with particular emphasis on reaction-intermediate analogs and other potent, reversible inhibitors. In: Böger, P., Sandmann, G. (Eds.), Target Sites of Herbicide Action. CRC Press, Boca Raton, FL, pp. 165-245.
24. Schuster, B., Rétey, J., 1995. The mechanism of action of phenylalanine ammonia-lyase: the role of prosthetic dehydroalanine. Proc. Natl. Acad. Sci. USA 92, 8433-8437.
25. Schwede, T.F., Rétey, J., Schulz, G.E., 1999. Crystal structure of histidine ammonia-lyase revealing a novel polypeptide modification as the catalytic electrophile. Biochemistry 38, 5355-5361.
26. Williams, J.W., Morrison, J.F., 1979. The kinetics of reversible tightbinding inhibition. Methods Enzymol. 63, 437-467.
27. Zoń, J., Laber, B., 1988. Novel phenylalanine analogues as putative inhibitors of enzymes acting on phenylalanine. Phytochemistry 27, 711-714.
28. Zoń, J., Amrhein, N., 1992. Inhibitors of phenylalanine ammonialyase: 2-aminoindan-2-phosphonic acid and related compounds. Liebigs Ann. Chem., 625-628.
29. Zoń, J., Amrhein, N., Gancarz, R., 2002. Inhibitors of phenylalanine ammonia-lyase: 1-aminobenzylphosphonic acids substituted in the benzene ring. Phytochemistry 59, 9-21.