| Identification | Back Directory | [Name]
2-amino-4-(hydroxymethylphosphinyl)butyric acid | [CAS]
51276-47-2 | [Synonyms]
C05042
HOE-866
HOE-35956
Phosphinothricin
IAJOBQBIJHVGMQ-UHFFFAOYSA-N
Phosphinothricin ammonium salt
2-Amino-4-(methylhydroxyphosphinyl)butyric acid
2-amino-4-(hydroxymethylphosphinyl)butyric acid | [EINECS(EC#)]
257-102-5 | [Molecular Formula]
C5H12NO4P | [MDL Number]
MFCD00211362 | [MOL File]
51276-47-2.mol | [Molecular Weight]
181.127 |
| Hazard Information | Back Directory | [Definition]
ChEBI: 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid is a non-proteinogenic alpha-amino acid that is 2-aminobutanoic acid which is substituted at position 4 by a hydroxy(methyl)phosphoryl group. It is a member of phosphinic acids and a non-proteinogenic alpha-amino acid. | [Enzyme inhibitor]
This dephospho transition-state analogue (FW = 177.10 g/mol; CAS 51276- 47-2) is naturally occurring glutamate analogue, first isolated from Streptomyces viridochromogenes. Phosphonothricin is a slow, tight-binding inhibitor of glutamine synthetase that binds at the glutamate binding site and stabilizes the flap of a glutamyl residue in a position blocking glutamate entry into the active site, thereby trapping the inhibitor on the enzyme. Phosphinothricin undergoes an ATP-dependent phosphorylation. Note: Phosphinothricin is a component of the antibiotics bialaphos and phosalacine. The monoammonium salt of the racemic compound, also called glufosinate-ammonium, is a post-emergent herbicide. | [Metabolic pathway]
When 14C-phosphinothricin [homoalanin-4-yl-
(methyl)phosphinic acid] is incubated in the cell
suspension cultures of soybean, wheat, and maize, in
maize cells which take up to 50% of the applied
radioactivity, four different metabolites are detected
which are identified as 4-methylphosphinico-2-oxo-
butyric acid, 4-methylphosphinico-2-hydroxybutyric
acid, 4-methylphosphinicobutyric acid, and 3-
methylphosphinicopropionic acid. In soybean and
wheat cultures, 10 and 6% of the applied radioactivity
is taken up, respectively. In soybean, only one
metabolite, 3-methylphosphinicopropionic acid, is
detected, whereas in wheat, 4-methyl-
phosphinicobutyric acid is additionally present. |
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