Inhibitors of phenylalanine ammonia-lyase: 1-aminobenzylphosphonic acids substituted in the benzene ring.
Dextrorotatory 1-amino-3',4'-dichlorobenzylphosphonic acid was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia-lyase both in vitro and in vivo from among the ring-substituted 1-aminobenzylphosphonic acids and other analogues of phenylglycine. A structure activity relationship analysis of the results obtained permits predictions on the geometry of the pocket of the enzyme and is a basis in the strategy of better inhibitor synthesis.
Zon
Jerzy
J
Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370, Wroclaw, Poland. zon@kch.ch.pwr.wroc.pl
Amrhein
Nikolaus
N
Gancarz
Roman
R
D000872:Anthocyanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019612:Fagopyrum / Q000378:metabolism; D007700:Kinetics; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
C450159:1-amino-3',4'-dichlorobenzylphosphonic acid; D000872:Anthocyanins; D001596:Benzylamines; D004791:Enzyme Inhibitors; D063065:Organophosphonates; D010650:Phenylalanine Ammonia-Lyase