173029-44-2Relevant academic research and scientific papers
A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate
Cheng, Janice M. H.,Dangerfield, Emma M.,Timmer, Mattie S. M.,Stocker, Bridget L.
supporting information, p. 2729 - 2736 (2014/05/06)
Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells. To investigate how modifications to the lipid tail or terminal sugar residu
Transition state analysis of Vibrio cholerae sialidase-catalyzed hydrolyses of natural substrate analogues
Chan, Jefferson,Lewis, Andrew R.,Indurugalla, Deepani,Schur, Melissa,Wakarchuk, Warren,Bennet, Andrew J.
experimental part, p. 3748 - 3757 (2012/05/04)
A series of isotopically labeled natural substrate analogues (phenyl 5-N-acetyl-α-d-neuraminyl-(2→3)-β-d-galactopyranosyl-(1→4) -1-thio-β-d-glucopyranoside; Neu5Acα2,3LacβSPh, and the corresponding 2→6 isomer) were prepared chemoenzymatically in order to
Synthesis of tri-, penta-, and heptasaccharides, functionalized with orthogonally N-protected amino residues at the reducing and non-reducing ends
Fyrner, Timmy,Svensson, Stefan C.T.,Konradsson, Peter
experimental part, p. 6712 - 6720 (2012/09/07)
The synthesis of four bifunctionalized orthogonally N-protected oligosaccharides derived from lactose and mannose, intended as cross-linking derivatives, is described. The aminosugar at the non-reducing end is derivatized with an N-Boc-protected glycine m
Synthesis of ganglioside G(M3) and G(M4) analogs having mimics of ceramide moieties and their binding activities with influenza virus A
Nagao,Nekado,Ikeda,Achiwa
, p. 1536 - 1542 (2007/10/03)
Ganglioside G(M4) (1) and G(M3) (2) analogs, which contain mimics of the ceramide moieties of gangliosides, were synthesized. The syntheses of 1 and 2 feature stereoselective glycosylation of methyl (phenyl 5-acetamido-4,7,8,9- tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-galacto-2-nonulopyranosid)onate (10) as the sialosyl donor with suitably protected galactose and lactose acceptors catalyzed by N-bromosuccinimide (NBS), iodine, and tetrabutylammonium trifluoromethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kinetically controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.
