100516-58-3Relevant articles and documents
Structure-activity relationship studies on the inhibition of the bacterial translation of novel Odilorhabdins analogues
Cao, Sha,Gualtieri, Maxime,Hjort, Karin,Hughes, Diarmaid,Huseby, Douglas L,Ikaunieks, Martins,Katkevics, Martins,Kukosha, Tatyana,Loza, Einars,Pantel, Lucile,Racine, Emilie,Ryabova, Victoria,Sarciaux, Matthieu,Serri, Marine,Shubin, Kirill,Suna, Edgars,Trufilkina, Nadezhda,Yadav, Kavita
, (2020/04/15)
A structure–activity relationship (SAR) study of NOSO-95179, a nonapeptide from the Odilorhabdin class of antibacterials, was performed by systematic variations of amino acids in positions 2 and 5 of the peptide. A series of non-proteinogenic amino acids was synthesized in high enantiomeric purity from Williams’ chiral diphenyloxazinone by highly diastereoselective alkylation or by aldol-type reaction. NOSO-95179 analogues for SAR studies were prepared using solid-phase peptide synthesis. Inhibition of bacterial translation by each of the synthesized Odilorhabdin analogues was measured using an in vitro test. For the most efficient analogues, antibacterial efficacy was measured against two wild-type Enterobacteriaceae (Escherichia coli and Klebsiella pneumoniae) and against an efflux defective E. coli strain (ΔtolC) to evaluate the impact of efflux on the antibacterial activity.
A New Method for Hydroxymethylene Peptide Isostere Synthesis: Asymmetric Synthesis of Statine
Williams, Robert M.,Colson, Pierre-Jean,Zhai, Weixu
, p. 9371 - 9374 (2007/10/02)
The asymmetric synthesis of (-)-Statine is described.The key step of the synthesis involves the coupling of hemi-acetal 6 with the ketene silyl acetal of methyl acetate.
Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates
Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo
, p. 1547 - 1557 (2007/10/02)
The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.