1-Aminobenzocyclobutene-1-phosphonic Acid and Related Compounds as Inhibitors of Phenylalanine Ammonia-Lyase.
Five new geminal aminocycloalkanephosphonic acids (4 - 8) containing both an aromatic ring and a cycloalkane ring were synthesized and evaluated as potential inhibitors of buckwheat phenylalanine ammonia-lyase (PAL). Within the set of compounds which are related to 2-aminoindane-2-phosphonic acid (AIP, 3), a known powerful inhibitor of PAL, racemic 1-aminobenzocyclobutene-1-phosphonic acid (4), was six times weaker than AIP as an in vitro inhibitor of buckwheat PAL, but six times stronger than AIP as an in vivo inhibitor of phenylalanine-derived anthocyanin synthesis in buckwheat.
Department of Thermodynamics, Theory of Machine and Thermal Systems, Faculty of Mechanical and Power Engineering, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego St., 50-370, Wrocław, Poland.
Jerzy
J
Zoń
Department of Thermodynamics, Theory of Machine and Thermal Systems, Faculty of Mechanical and Power Engineering, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego St., 50-370, Wrocław, Poland.
Piotr
P
Miziak
D000872:Anthocyanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D019612:Fagopyrum / Q000201:enzymology; D007189:Indans; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors*; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000494:pharmacology*
D000872:Anthocyanins; D004791:Enzyme Inhibitors; D007189:Indans; D010757:Phosphorous Acids; C006545:2-aminoindan; D010650:Phenylalanine Ammonia-Lyase
2-Aminoindane-2-phosphonic acid; 7-Aminobicyclo[4.2.0]octa-1,3,5-triene-7-phosphonic acid; 8-Aminobicyclo[4.3.0]nona-1,3,5-triene-8-phosphonic acid; Buckwheat; PAL Inhibitor