Inhibition of rat liver glutamine synthetase by phosphonic analogues of glutamic acid

The Metabolites of the Herbicide L-Phosphinothricin (Glufosinate) (Identification, Stability, and Mobility in Transgenic, Herbicide-Resistant, and Untransformed Plants)

“…The toxicology of t-Pt has been intensively analyzed (Lejczak et al, 1981;Lacoste et al, 1985;Dom et al, 1986;Logusch et al, 1989) and was summarized by Ebert et al (1990). It is safe under the conditions of recommended use, but, according to European Economic Community directive 83/467/EEC, it has to be classified as harmful on the basis of testing for acute oral toxicity (Ebert et al, 1990).…”

Evaluation of the amino acid binding site of Mycobacterium tuberculosis glutamine synthetase for drug discovery

“…In fact a number of inhibitors, including MSO, 8 or its diastereomeric mixture L-(SR), 8,11,13,23 PPT, 8,19,20,[22][23][24][25]28 3, 19,20 and 4 29,35 have shown inhibitory activity when tested on both bacterial and eukaryotic GSs. Therefore a literature search was performed to identify known GS inhibitors for both eukaryotic and prokaryotic enzymes.…”

“…Several functional groups, including a carboxylic acid, a thioether, a sulfoxide, a sulfonamide and a phosphonate ester, were investigated as R 2 substituents. The compounds were synthesized from glycine (24)(25)(26)(27)(28) or from L- (29)(30)(31)(32)(33) or D-serine (34)(35)(36)(37)(38), as described in the experimental section. The desired products were prepared via a CuI catalyzed N-arylation of glycine, D-and L-serine, using K 2 CO 3 as a base, with an appropriately substituted arylbromide (Scheme 2).…”

“…[10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] Much effort has been invested in developing GS inhibitors not only for antibacterial research, but also for weed control, 20,25,[30][31][32] since GS is a key enzyme in ammonia assimilation in plants. However, no inhibitor has shown improved activity compared to MSO or PPT.…”

Structure of 4-amino-4-phosphonobutyric acid

“…These possess antibiotic properties (Kondo, Shomura, Ogawa, Tsuruoka, Watanabe, Totzukawa, Suzuki, Moriyama, Yoshida, Inouye & Niida, 1973) and antiviral (Fukuyasu, Oya, Kawakami, Kikuchi, Shomura, Tsuruoka, Watanabe, Kazuho, Inouye & Sekizawa, 1978), neuroactive (De TinguY-Moreaud, Bioulac & Neuzil, 1981) and herbicidal activities (Rupp, Finke, Beringer & Lagenlueddeke, 1977). Except for a single report (Lejczak, Starzemska & Mastalerz, 1981)that the ct-aminophosphonic acid structurally related to glutamate is a weak inhibitor of glutamine synthetase, nothing has been reported as yet about the biological 0108-2701/87/020289-03501.50 activity of the a-phosphono analogues of glutamic acid.…”