30077-45-3Relevant academic research and scientific papers
Semisynthesis of the organoarsenical antibiotic arsinothricin
Suzol, Sazzad H.,Howlader, A. Hasan,Galvan, Adriana E.,Radhakrishnan, Manohar,Wnuk, Stanislaw F.,Rosen, Barry P.,Yoshinaga, Masafumi
, p. 2809 - 2813 (2020)
Arsinothricin [AST (1)], a new broad-spectrum organoarsenical antibiotic, is a nonproteinogenic analogue of glutamate that effectively inhibits glutamine synthetase. We report the chemical synthesis of an intermediate in the pathway to 1, hydroxyarsinothricin [AST-OH (2)], which can be converted to 1 by enzymatic methylation catalyzed by the ArsM As(III) Sadenosylmethionine methyltransferase. This is the first report of semisynthesis of 1, providing a source of this novel antibiotic that will be required for future clinical trials.
Synthesis of the organoarsenical antibiotic arsinothricin and derivatives thereof
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Page/Page column 26; 28, (2021/03/03)
The subject invention provides methods and procedures for synthesis and/or semi-synthesis of the novel antibiotic arsinothricin (AST) and derivatives. Arsinothricin (AST), a new broad-spectrum organoarsenical antibiotic, is a non-proteinogenic analog of glutamate that effectively inhibits glutamine synthetase. The subject invention provides chemical synthesis of an intermediate in the pathway of AST synthesis, hydroxyarsinothricin (AST-OH), which can be converted to AST by enzymatic methylation catalyzed by the ArsM As(III) S-adenosylmethionine methyltransferase. The methods provide a source of the novel antibiotic that will be required for future clinical trials. The subject invention also provides AST derivatives as a new class of antibiotics.
THE USE OF CHLOROALKYLDICHLOROARSINES IN HIBRID LIGAND SYNTHESIS. THE PREPARATION OF BUT-3-ENYLBIS(3-DIMETHYLARSINOPROPYL)ARSINE AND 3-DIMETHYLARSINOPROPYLBIS(BUT-3-ENYL)ARSINE, AND THEIR REACTION WITH NICKEL(II) SALTS TO FORM PENTACOORDINATE COMPLEXES. NOVEL NICKEL(II)-OLEFIN BONDS
Ashmawy, Fathy M.,Benn, F. Roger,McAuliffe, Charles A.,Watson, David G.
, p. 65 - 80 (2007/10/02)
Routes have been developed to the hitherto unobtainable arsine-olefin ligands (CH2=CHCH2CH2)nAs(CH2CH2CH2AsMe2)3-n (n= 1, tasol, but-3-enylbis(3-dimethylarsinopropyl)arsine; n= 2, dasdol, 3-dimethylarsinopropylbis(but-3-enyl)arsine) by making use of the difference in reactivity between the Cl-C and As-Cl bonds in the precursor Cl(CH2)mAsCl2 (m = 2,3) molecules.Thus, the triarsine obtained by reaction of 2-chloroethyldichloroarsine with the Grignard reagent of 3-chloropropyldimethylarsine yields 2-chloroethylbis(3-dimethylarsinopropyl)arsine, from wich tasol is obtainable by subsequent reaction with either the Grignard reagent of vinyl bromide or, preferably, with vinyllithium.Similarly, 3-chloropropyldichloroarsine reacts with the Grinard reagent of 4-chlorobut-1-ene to form 3-chloropropylbis(but-3-enyl)arsine which, on reaction with sodium dimethyarsenide yields dasdol.The tasol ligand reacts with nickel(II) salts to form + (X = Cl, Br) and , the former are trigonal bipyramidal and contain a nickel(II)-olefin bond, and the latter are square pyramidal containing a coordination sphere.In addition, tasol forms a number of polynuclear complexes with nickel(II).The dasdol ligand acts as a bidentate arsine form only +.The formation of novel nickel(II)-olefin bonds in the + cation is discussed.
