35597-43-4 Usage
Description
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.
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).
Definition
ChEBI: A tripeptide comprising one L-phosphinothricyl and two L-alanyl units joined in sequence.
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.
