62098-31-1Relevant academic research and scientific papers
Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from d-glucosamine
Glego?a, Katarzyna,Framery, Eric,Goux-Henry, Catherine,Micha? Pietrusiewicz,Sinou, Denis
, p. 7133 - 7141 (2007)
The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been in
Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases
DiFrancesco, Benjamin R.,Morrison, Zachary A.,Nitz, Mark
, p. 5631 - 5643 (2018/10/24)
The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).
Simple d-glucosamine-based phosphine-imine and phosphine-amine ligands in Pd-catalyzed asymmetric allylic alkylations
Glego?a, Katarzyna,Johannesen, Sine A.,Thim, Laura,Goux-Henry, Catherine,Skrydstrup, Troels,Framery, Eric
supporting information; experimental part, p. 6635 - 6638 (2009/04/06)
A new family of phosphine-imine and phosphine-amine ligands based on d-glucosamine were synthesized in order to probe previous asymmetric allylic alkylation results with those of disaccharide ligands of the same class. In most cases, good-to-excellent activities and enantioselectivies were observed with these ligands with ee's reaching up to 87% in the Pd-catalyzed allylic alkylation reaction of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate as the nucleophile.
