4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH 化学構造式

4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH

化学名:4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH

CAS番号.35597-43-4

英語名:BIALAPHOS

CBNumberCB7329454

MFC11H22N3O6P

MW323.28

MOL File35597-43-4.mol

别名

ビアラホス

抗生物質SF-1293

4-(メチルホスホニル)-L-Abu-L-Ala-L-Ala-OH

4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH物理性質

融点	159-161 C
沸点	793.2±60.0 °C(Predicted)
比重(密度)	1.330±0.06 g/cm3(Predicted)
貯蔵温度	Store dry at -4
酸解離定数(Pka)	2.86±0.50(Predicted)

安全性情報

主な危険性	Xn
Rフレーズ	20/21/22-36/37/38
Sフレーズ	26-36

危険有害性情報のコード(GHS)

4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH 化学特性,用途語,生産方法

説明
Bilanofos is a natural product formed during the fermentation of Streptomyces hygroscopicus. It is readily soluble in water and insoluble in organic solvents such as acetone, ethanol, benzene, and hexane (9).
Bilanophos is a GS inhibitor. In the plant, bilanofos is metabolized to L-glufosinate, which inhibits the enzyme GS. Ammonium ions rapidly accumulate in the plant, and photosynthesis is inhibited, leading to rapid death of the plant. It is inactivated in soil.
来歴
Bialaphos[peptide derivative of PPT (PPT linked to two L-alanine moieties)] was originally isolated from cultures of Streptomyces viridochromogenes (87) and Streptomyces hygroscopicus (88). L-PPT is the natural isomer, and it was the first natural amino acid found to contain a phosphinic group. PPT strongly inhibited glutamine synthetase activity in E. coli (87), and Hoechst Ag patented it as a herbicide after its phytotoxicity was discovered (89). Bialaphos was patented as a herbicide (90) and is marketed in Japan (91). Glufosinate (ammonium salt of PPT) is the synthesized commercial product. Bialaphos is hydrolyzed by plant and soil microbial peptidases to yield the active herbicide (PPT) (92–94). PPT is also rapidly degraded, with half-life of 4 to 7 days in soils (95). In a test of 300 bacterial isolates from soil, all strains degraded L-PPT to the 2-oxo analog of PPT via transamination (96).
定義
ChEBI: A tripeptide comprising one L-phosphinothricyl and two L-alanyl units joined in sequence.
Origin
The compound was launched as a nonselective contact herbicide in 1984.
代謝経路
When 14C-bialaphos [L-2-amino-4- [(hydroxy)(methyl)phosphinoyl]butyryl-L-alanyl-L- alanine] is administered in an aqueous solution to mice, the metabolite of bialaphos which is identified as 2-amino-4-[(hydroxy)(methyl)phosphinoyl]butyric acid is excreted in the feces and urine.
代謝
The major metabolite following oral administration in the mouse was 2-amino-4- (hydroxy)(methyl)phosphinyl)butyric acid, which was eliminated in feces.

4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH 生産企業

35597-43-4, 4-(メチルヒドロキシホスフィニル)-L-Abu-L-Ala-L-Ala-OH キーワード

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