79781-71-8Relevant academic research and scientific papers
Gram scale synthesis of A (type 2) and B (type 2) blood group tetrasaccharides through 1,6-anhydro-N-acetyl-β-D-glucosamine
Tyrtysh, Tatiana V.,Korchagina, Elena Yu.,Ryzhov, Ivan M.,Bovin, Nicolai V.
, p. 65 - 84 (2017/07/26)
Gram scale synthesis of A (type 2) and B (type 2) tetrasaccharides in the form of 3-aminopropyl glycosides is proposed starting from 3-O-benzoyl-1,6-anhydro-N-acetylglucosamine. Its galactosylation followed by re-protection gave lactosamine derivative with single free 2′-OH group in total yield 75%. Standard fucosylation and next run of re-protection in total yield 88% gave a trisaccharide Fuc-Gal-anhydroGlcNAc with single free 3′-OH group. Its standard α-galactosylation gave protected B (type 2) tetrasaccharide. For synthesis of correspondent A tetrasaccharide seven different 2-azido-2-deoxygalactosyl (GalN3) donors were tested: 6-O-acetyl-3,4-O-isopropylidene-GalN3 thioglycoside was shown to provide the best yield (89%) and stereoselectivity (α/β = 24:1). Further 1,6-anhydro cycle opening, spacer-arming and complete deprotection resulted in the target 3-aminopropyl glycosides of A (type 2) and B (type 2) tetrasaccharides, yields 87 and 85% correspondingly.
Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapG(J)96 from Escherichia coli
Hansen, Henrik C.,Magnusson, Goeran
, p. 233 - 242 (2007/10/03)
The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2(trimethylsilyl)ethyl (α-D-galactopyranosyl)-(1→4)- β-d-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K(rel); relative to the reference inhibitor) were: 157, 13, and 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside.
SYNTHESE DER TETRA- UND TRISACCHARID-SEQUENZEN VON ASIALO-GM1 UND -GM2. LENKUNG DER REGIOSELEKTIVITAET DER GLYCOSIDIERUNG VON LACTOSE
Paulsen, Hans,Paal, Michael
, p. 39 - 62 (2007/10/02)
A regioselective β-glycosidation of lactose derivatives unsubstituted at OH-3' and -4' is possible, depending on the catalyst system applied.With silver silicate or silver carbonate as catalyst under hetrogeneous conditions, β-glycosidation occured selectively at the less reactive OH-4'group of the acceptor, whereas with trimethylsilyl triflate or soluble mercury salt as catalyst under homogeneous conditions, it occured almost exclusively at the more reactive OH-3' group.The reactivity of the glycosyl donor, acceptor, and catalyst had to be properly matched for successful regioselective coupling.In this way, the trisaccharide unit of asialo-GM2-ganglioside, O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1--4)-(β-D-galactopyranosyl-(1--4)-D-glucopyranose, and the tetrasaccharide unit of asialo-GM1-ganglioside, O-(β-D-galactopyranosyl)-(1--3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1--4)-(β-D-galactopyranosyl)-(1--4)-β-D-glucopyranose were synthesized.This new method constitutes a very useful approach in the field of ganglioside synthesis.
STEREOSELECTIVITY OF GLYCOSYLATION WITH DERIVATIVES OF 2-AZIDO-2-DEOXY-D-GALACTOPYRANOSE. THE SYNTHESIS OF A DETERMINANT OLIGOSACCHARIDE RELATED TO BLOOD-GROUP A (TYPE 1)
Bovin, Nikolai V.,Zurabyan, Sergei E.,Khorlin, Anatoly Ya.
, p. 23 - 36 (2007/10/02)
The stereoselective glycosylation of a model alcohol (cyclohexanol) by derivatives of 2-azido-2-deoxy-D-galactopyranose was studied under various conditions. 2-Azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride (9) was found to be the most eff
