35597-43-4 Usage
Description
Bialaphos is a natural product produced during the fermentation of Streptomyces hygroscopicus. It is water-soluble and insoluble in organic solvents such as acetone, ethanol, benzene, and hexane. Bialaphos is a GS inhibitor, and in plants, it is metabolized to L-glufosinate, which inhibits the enzyme GS. This leads to the rapid accumulation of ammonium ions in the plant and inhibition of photosynthesis, resulting in the rapid death of the plant. Bialaphos is inactivated in soil.
Usage:
Used in Agriculture:
Bialaphos is used as a herbicide for controlling broadleaf and grassy weeds in various crops such as rice, wheat, and corn. It targets the enzyme GS, which is essential for plant growth and survival, leading to the rapid death of the weeds without harming the crops.
Used in Pharmaceutical Industry:
Bialaphos is used as a pharmaceutical agent for the development of drugs targeting the enzyme GS. This enzyme is involved in the biosynthesis of amino acids and other essential cellular processes, making it a potential target for the treatment of various diseases and disorders.
Used in Environmental Management:
Bialaphos can be used in environmental management for the control of invasive plant species and the management of aquatic weeds in water bodies. Its ability to target the enzyme GS in plants makes it an effective tool for controlling the growth and spread of unwanted plant species.
History
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).
Metabolic pathway
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.
Metabolism
The major metabolite following
oral administration in the mouse was 2-amino-4-
(hydroxy)(methyl)phosphinyl)butyric acid, which was
eliminated in feces.
Check Digit Verification of cas no
The CAS Registry Mumber 35597-43-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,5,9 and 7 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 35597-43:
(7*3)+(6*5)+(5*5)+(4*9)+(3*7)+(2*4)+(1*3)=144
144 % 10 = 4
So 35597-43-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1
35597-43-4Relevant articles and documents
Total synthesis and enzyme-substrate interaction of D-, DL-, and L-Phosphinotricine, 'bialaphos' (SF-1293) and its cyclic analogues
Natchev, Ivan A.
, p. 125 - 131 (2007/10/02)
DL-Phosphonotricine (3) and its cyclic analogue (4) have been synthesized using the four-component isocyanide condensation of Ugi and Ugi-analogous three-component condensation, respectively. High selectivity of the enzyme-substrate interaction was established with the enzymes α-chymotrypsin, phosphodiesterase I, and alkaline mesintericopeptidase, as well as by separation of the racemic mixture to optical antipodes by the α-chymotripsin. The tripeptide 'bialaphos' (11) and its D-antipode (11a) have been synthesized by the method of activated esters, and the cyclic analogue (15) by the DCC method. It was found that the phospholane L-(5) and the tripeptide (18) exhibit anti-tumour activity.
