Methyl 3,4,6-tri-O-benzyl-2-O-[6-O-(tert-butyldiphenylsilyl)-α-d-mannopyranosyl]-α-d-mannopyranoside (2) was synthesized by treatment of methyl 3,4,6-tri-O-benzyl-2-O-α-d-mannopyranosyl-α-d-mannopyranoside with tert-butylchlorodiphenylsilane in the presence of imidazole. Isopropylidenation, ...

For the first time a monosaccharide (methyl α-d-mannopyranoside) has been used as starting material for the synthesis of novel σ-receptor ligands. The hept-3-ulopyranoside dimethyl ketals 14 and 15 were obtained from the nitrile 7 via two synthetic routes. After selective hydrolysis of the ket...

Reaction of p-trifluoroacetamidophenyl 2,4-di-O-benzyl-α-d-mannopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-α-d-mannopyranosyl chloride gave a trisaccharide derivative which was O-deacetylated and then treated with ethyl 2,3,4-tri-O-benzyl-6-O-dibenzyloxyphosphoryl-1-thio-α-d- mannopyranosi...

Treatment of benzyl α-(1) and methyl β-d-mannopyranoside (2) with α,α-dimethoxytoluene gave the exo and endo isomers (3,5 and 4,6) of the dibenzylidene derivatives of 1 and 2. Hydrogenolysis of the exo isomers (3 and 5) with a molar equivalent of AlH2Cl gave the 3-0-benzyl-4,6-0-benzylidene ...

Reaction of mono-, di-, and trisaccharide derivatives of methyl β-d- and octyl β-d-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplén conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds...

A panel of analogs of the disaccharide α-d-Manp-(1→6)-α-d-Manp-OOctyl, a known acceptor substrate for a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in the assembly of the α-(1→6)-linked mannan core of mycobacterial lipoarabinomannan, has been synthesized. ...

Acetylation of benzyl α-D-mannopyranoside with acetic anhydride-sodium acetate at room temperature gave crystalline benzyl 2,3,6-tri-O-acetyl-α-D-manno-pyranoside (25%) and benzyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (≈65%). Similar esterification of benzyl β-D-glucopyranoside yielded...

The synthesis of a series of alkyl (having from C6 to C20 aglycones), cyclohexyl, and cyclohexylalkyl α-d-mannopyranosides, 6-deoxygenated analogs, thioglycosides, and sulfones derived thereof, is reported. Here, under the in vitro assay conditions used, none of the 15 tested compounds acted as...

A novel 1,6-α-d-mannosidase was produced by Aspergillus phoenicis grown on a commercial manno-oligosaccharide preparation in liquid culture. The enzyme hydrolysed only α-d-Manp-(1→6)-d-Manp and did not act on α-d-Manp-(1→2)-d-Manp, or α-d-Manp-(1→3)-d-Manp. The 1,6-α-d-mannosidase was us...

Instead of an enzyme-assisted reverse hydrolysis reaction for the synthesis of manno-oligosaccharides, we propose here a versatile new approach. By Fischer type glycosylation, a d-mannose solution of extremely high concentration (approximately 83% (w/w)) was incubated at 60 °C for 65 h in 0.5 M...

d-Xylobiose hexaacetate and d-mannobiose octaacetate were obtained from xylan and mannan digests, respectively, by acetylation followed by chromatographic separation. Selective anomeric deacetylation of each peracetate, followed by 2,4-dinitrophenylation and subsequent de-protection gave 2,4-din...

Salmonella spp. is one of the major causes of food-borne illness in humans, and Salmonella enteritidis (SE) infection in commercial poultry is a world-wide problem. Here we have investigated the in vitro immune-modulating effects of β 1-4 mannobiose (MNB), which was previously found to prevent ...

ABSTRACTBackground: Dietary supplementation with unique prebiotic nondigestible carbohydrates has been shown to suppress allergy. In the present study, the prophylactic efficacy of a disaccharide p-1, 4 mannobiose (MNB) in a BALB/C mouse model of intranasally-induced pollen allergy was character...

ABSTRACTBackground: Nutritional prebiotic supplementation represents an attractive approach for interventions of allergy. In this study, the potential therapeutic effect of β-1, 4 mannobiose (MNB) in a murine model of cedar polli- nosis was investigated.Methods: Groups of Balb/c mice were intra...

The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-α-d-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-α-d-mannopyranosyl)-α-d-mannopyranoside (α-1,3-Man), were synthesized respectively....

Glycoside hydrolase family 130 consists of phosphorylases and hydrolases for β-mannosides. Here, we characterized β-1,2-mannobiose phosphorylase from Listeria innocua (Lin0857) and determined its crystal structures complexed with β-1,2-linked mannooligosaccharides. β-1,2-Mannotriose was boun...

Protected derivatives of the title carba-trisaccharide 1, and carba-disaccharides 4 and 6 have been synthesized by conventional glycosylation of the precursors 89, or 22 of 5a-carba-α-d-mannopyranose with sugar halides. These are carba-sugar analogues of the oligosaccharide chains frequently oc...

The 8-methoxycarbonyloctyl glycosides of α-d-mannopyranose, 2-O-α-mannopyranosyl-α-d-mannopyranose, β-d-galactofuranose, and 3-O-β-d-galactofuranosyl-α-d-mannopyranose were prepared as intermediates for the synthesis of complexes with the general structure mono-(or di-)saccharide-lipid spa...

A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldeh...

A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl–camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor–pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β...