7464-38-2Relevant articles and documents
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Haskins et al.
, p. 1668,1669 (1947)
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Aromatic thioglycoside inhibitors against the virulence factor LecA from Pseudomonas aeruginosa
Rodrigue, Jacques,Ganne, Geraldine,Blanchard, Bertrand,Saucier, Catherine,Giguere, Denis,Shiao, Tze Chieh,Varrot, Annabelle,Imberty, Anne,Roy, Rene
, p. 6906 - 6918 (2013/10/08)
Three small families of hydrolytically stable thioaryl glycosides were prepared as inhibitors of the LecA (PA-IL) virulence factor corresponding to the carbohydrate binding lectin from the bacterial pathogen Pseudomonas aeruginosa. The monosaccharidic arylthio β-d-galactopyranosides served as a common template for the major series that was also substituted at the O-3 position. Arylthio disaccharides from lactose and from melibiose constituted the other two series members. In spite of the fact that the natural ligand for LecA is a glycolipid of the globotriaosylceramide having an α-d-galactopyranoside epitope, this study illustrated that the β-d-galactopyranoside configuration having a hydrophobic aglycon could override the requirement toward the anomeric configuration of the natural sugar. The enzyme linked lectin assay together with isothermal titration microcalorimetry established that naphthyl 1-thio-β-d-galactopyranoside (11) gave the best inhibition with an IC 50 twenty-three times better than that of the reference methyl α-d-galactopyranoside. In addition it showed a KD of 6.3 μM which was ten times better than that of the reference compound. The X-ray crystal structure of LecA with 11 was also obtained.
Odorless preparation of thioglycosides and Thio-Michael adducts of carbohydrate derivatives
Mukherjee, Chinmoy,Misra, Anup Kumar
, p. 213 - 221 (2008/02/12)
A general, odorless, one-pot methodology has been developed for the preparation of 1,2-trans-thioglycosides and thio-Michael addition products of carbohydrate derivatives through triphenyl phosphine-mediated cleavage of disulfides and reaction of the thio
