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Inhibitors of Phenylalanine Ammonia‐Lyase (PAL): Synthesis and Biological Evaluation of 5‐Substituted 2‐Aminoindane‐2‐phosphonic Acids
Author(s) -
Zoń Jerzy,
Miziak Piotr,
Amrhein Nikolaus,
Gancarz Roman
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590089
Subject(s) - chemistry , phenylalanine ammonia lyase , phenylalanine , ammonia , stereochemistry , lyase , enzyme , biosynthesis , in vitro , in vivo , biochemistry , amino acid , microbiology and biotechnology , biology
A series of 5‐substituted derivatives of the potent phenylalanine ammonia‐lyase (PAL) inhibitor 2‐aminoindane‐2‐phosphonic acid (AIP; 2 ) were synthesized. The AIP analogues 3 – 7 , with additional NO 2 , NH 2 , Me, Br, and OH groups, respectively, were tested as in vitro inhibitors of buckwheat PAL, and as in vivo inhibitors of anthocyanin biosynthesis. Within this series, the racemic 5‐bromo ( 6 ) and 5‐methyl ( 7 ) congeners were biologically most active ( Table ), although being ca. one order of magnitude less potent than AIP proper.