title: Inhibitors of phenylalanine ammonia-lyase: substituted derivatives of 2-aminoindane-2-phosphonic acid and 1-aminobenzylphosphonic acid.
abstract: Six derivatives of 2-aminoindane-2-phosphonic acid and 1-aminobenzylphosphonic acid were synthesized. The compounds were tested both as inhibitors of buckwheat phenylalanine ammonia-lyase (in vitro) and as inhibitors of anthocyanin biosynthesis (in vivo). (+/-)-2-Amino-4-bromoindane-2-phosphonic acid was found to be the strongest inhibitor from investigated compounds. The results obtained are a basis for design of phenylalanine ammonia-lyase inhibitors useful in the enzyme structure studies in photo labelling experiments.
authors.affiliation: Faculty of Chemistry, Department of Medicinal Chemistry and Microbiology, Wrocław University of Technology, Wybrzeze Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Miziak
authors.forename: Jerzy
authors.initials: J
authors.lastname: Zoń
authors.forename: Nikolaus
authors.initials: N
authors.lastname: Amrhein
authors.forename: Roman
authors.initials: R
authors.lastname: Gancarz
mesh_terms: D000588:Amines / Q000494:pharmacology; D001593:Benzyl Compounds / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D019612:Fagopyrum / Q000201:enzymology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors*; D010940:Plant Proteins / Q000037:antagonists & inhibitors
chemical_list: D000588:Amines; D001593:Benzyl Compounds; D004791:Enzyme Inhibitors; D063065:Organophosphonates; D010940:Plant Proteins; D010650:Phenylalanine Ammonia-Lyase