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Inhibitors of Phenylalanine Ammonia‐Lyase: 2‐Aminoindan‐2‐phosphonic Acid and Related Compounds
Author(s) -
Zoń Jerzy,
Amrhein Nikolaus
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201107
Subject(s) - chemistry , phenylalanine , ammonia , alkylation , enzyme , phenylalanine ammonia lyase , benzene , stereochemistry , in vivo , liquid ammonia , organic chemistry , biochemistry , amino acid , catalysis , microbiology and biotechnology , biology
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(bromomethyl)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 inhibitor of the plant enzyme phenylalanine ammonia‐lyase (EC 4.3.1.5) both in vitro and in vivo. Of the related 2‐aminoindan‐2‐carboxylic acid ( 4 ), compound 5 , and 1‐aminocyclopentylphosphonic acid ( 6 ), only 4 inhibited the enzyme but was far less inhibitory than 3 .