Phosphinothricins

L-alanyl-L-2,3-epoxy-4-oxohexahydrophenylalanine [29393-20-2] C22H2gN20, inhibit glutamine metaboHsm, as does bialaphos as a source of the amino acid L-phosphinothricin [35597-44-5] 0 11 2 04 . 

Although the antibacterial and antifungal activities of bialaphos and phosphinothricin were not found to be usehil, the two agents were later used as biodegradeable, relatively nonselective, postemergent herbicides. Glutamine synthetase inhibition is toxic to plants because the enzyme is key to ammonia assimilation. There is some selectivity for individual plant species as shown by the LD for bialaphos ranging from 0.125 to 8.5 kg/ha (301—303). 

Bialaphos, produced by fermentation of S. hjgroscopicus is sold in Japan. Racemic phosphinothricin [53369-07-6] C H22N04P, produced chemically (304,305), is sold in the United States and elsewhere as the monoammonium salt called glufosinate-ammonium [77182-82-2] C H22N04P H N, or Total or Basta (formerly Hoe 661, Hoe 39866). 

Office of Prevention, Protection and Toxic Substances Phosphinothricin acetyltransferase Phenoxybenzoic acid Polychlorinated biphenyl Polymerase chain reaction Polygalacturonase Acid dissociation constant... 

CrylF protein, phosphinothricin acetyltransferase (PAT) 5-Enolpymvylshildmate-3-phosphate synthase (EPSPS)... 

Anionic trivalent phosphorus reagents have also been found to be of use in the preparation of some intriguing species. For example, an approach to L-phosphinothricin and related materials has been accomplished by addition of the conjugate base of alkyl methylphos-phonites to protected L-vinylglycine species (Equation 3.31).450 The starting protected L-vinylglycine species are readily available from l-methionine and L-glutamic acid. 

Maier, L. and Rist, G., Organic phosphorus compounds. 77. Synthesis and properties of phosphinothricin homologs and analogs, Phosph. Sulf, 17, 21, 1983. 

Zeiss, H.J., Enantioselective synthesis of L-phosphinothricin. III. Enantio-selective synthesis of L-phosphinothricin from L-methionine and L-glutamic acid via L-vinylglycine, Tetrahedron, 48, 8263, 1992. 

Phosphine complexes, osmium, 19 642 Phosphine coordination complexes, of uranium, 25 436 Phosphine derivatives, 19 28 Phosphine oxide(s), 11 495-496 19 66 predicted deviations from Raoult s law based on hydrogen-bonding interactions, 8 814t in salicylic acid manufacture, 22 8 Phosphine oxide diols/triols, 11 501 Phosphine selenides, 22 90 Phosphinic acid, 19 20, 54-55 Phosphinic anhydride, 11 499 Phosphinothricin acetyltransferase (PAT) proteins, 13 360 Phosphite esters, 19 20 Phosphites, in VDC polymer stabilization, 25 720... 

Both (R)- and (S)-amino transferase are available forthe synthesis of enantiomerically pure amines from racemic amines. Degrees of conversion were at or close to 50% for resolutions, and enantioselectivities customarily reached > 99% e.e. for the amine product from both resolutions or syntheses from ketones (Stirling, 1992 Matcham, 1996). The donor for resolutions of amine racemates was usually pyruvate whereas either isopropylamine or 2-aminobutane served as donors for reduction of ketones. The products range from i- and D-amino acids such as i-aminobutyric acid (see Section 7.2.2.6) and i-phosphinothricin (see Section 7.4.2) to amines such as (S)-MOIPA (see Section 7.4.2). 

Applications of Transaminases towards Crop Protection Agents L-Phosphinothricin and (S)-MOIPA... 

Figure 7.31 Coupled process for the herbicide ingredient L-phosphinothricin with transaminases (Drauz, 2002).

S Omura, M Murata, H Hanak, K Hinotozawa, R Oiwa, H Tanaka. Phosalacine, a new herbicidal antibiotic containing phosphinothricin. Fermentation, isolation, biological activity and mechanism of action. J Antibiot 37 829-835, 1984. 

I) The most obvious is the direct use of the allelochemicals as new herbicides, targeting new sites of action. Few successful examples can be mentioned but, among them, glyphosate (1) [the synthetic version of phosphinothricin... 

---