- Phosphonic analogues of phenylalanine and histidine as strong inhibitors of phenylalanine and histidine ammonia-lyases
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Syntheses of phosphonic analogues of phenylalanine (5) and histidine (7) as well as their biological activities as phenylalanine and histidine ammonialyases inhibitors have been discussed.
- Zon, Jerzy
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- Inhibitors of Phenylalanin Ammonia-Lyase: 2-Aminoindan-2-phosphonic Acid and Related Compounds
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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. Key Words: 2-Aminoindan-2-phosphonic acid/Enzyme inhibition/Phenylalanine ammonia-lyase
- Zon, Jerzy,Amrhein, Nikolaus
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p. 625 - 628
(2007/10/02)
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