Inhibitors of Phenylalanine Ammonia‐Lyase: 2‐Aminoindan‐2‐phosphonic Acid and Related Compounds

Abstract

Key Words: 2-Aminoindan-2-phosphonic acid/Enzyme inhibition/Phenylalanine ammonia-lyase 2-Aminoindan-2-phosphonic acid (3) was synthesized for the first time both directly from 2-indanone (7) as well as by alkylation of ethyl diethoxyphosphorylacetate with 1,2-bis(bro-momethy1)benzene (9) via 10 -12, respectively. 2-Hydroxyindan-2-phosphonic acid (5) was obtained also from 7 via its diisopropyl ester 8. Compound 3 was found to be a potent

Restoration of secondary metabolism in birch seedlings relieved from PAL-inhibitor

“…The trays were randomly selected into four groups (n = 5 in each group): a control (0 lM of AIP) and three AIP treatments (5, 15 and 30 lM of AIP), hereafter referred to as AIP5, AIP15 and AIP30, also for the period in AIPfree medium. The AIP was synthesized as in Zoń and Amrhein (1992). The seedlings grew in AIP-medium for 23 days, before being changed to AIP-free conditions; the first day (day 0) of the reversibility experiment.…”

“…AIP is a slow binding inhibitor of PAL, and the inhibition has been shown to be reversible in vitro in a pure, clearly defined PAL preparation (Appert et al 2003). AIP has been shown to inhibit the accumulation of many kinds of phenolic compounds (Zoń and Amrhein 1992;Reuber et al 1993;Gitz et al 1998;Julkunen-Tiitto 2000, 2003). Growth responses to AIP have varied, showing decreases (Reuber et al 1993;Janas et al 1998), increases (Gitz et al 1998;Ruuhola and Julkunen-Tiitto 2003) or no effect (Ruuhola and Julkunen-Tiitto 2000;Janas et al 2002).…”

“…Different inhibitors of PAL have been tested (see Appert et al (2003) for an overview), and among these 2-aminoindan-2-phosphonic acid monohydrate (AIP) was found to be particularly effective and selective, both in vivo and in vitro (Zoń and Amrhein 1992;Zoń et al 2004). AIP is a slow binding inhibitor of PAL, and the inhibition has been shown to be reversible in vitro in a pure, clearly defined PAL preparation (Appert et al 2003).…”

Growth-Retarding Effect of 2-Aminoindan-2-phosphonic Acid on Spirodela punctata

“…aminooxy and phosphonic, L-␣-aminooxy-␤-phenylpropionic acid (AOPP), 2-aminoindan-2-phosphonic acid (AIP) (Fig. 1), 1-amino-2-phenylethylphosphonic acid (PheP), and 1-amino-3-phenylpropylphosphonic acid (PhPP) (Amrhein and Gödecke 1977, Janas et al 1985, Janas and Olechnowicz 1994, Zoń and Amrhein 1992. Specific enzyme inhibitors are valuable tools in the study of in vivo metabolic pathways.…”

“…Using AIP, a potent PAL inhibitor (K i ‫ס‬ 0.08 M for buckwheat PAL), phenylpropanoid inhibition of buckwheat and rye seedlings was observed (Reuber et al 1993, Zoń andAmrhein 1992). This compound had a negative effect on growth, fresh weight, and root development, and it reduced the content of phenylpropanoids in primary leaves of rye (Secale cereale L.) and suspension culture of Lithospermum erythrorhizon Sieb.…”