(2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction mixture (100 mL, 100 mM Tris, pH 7.5, 10 mM MgCl2, 10 mM MnCl2, 5 mM EDTA, 5 ThM NaN3, 1 mm ATPe 0.01 mM theophylline and 0.03 mM 2, 3-dimercaptopropanol) containing α-methyl-D-mannopyranoside (0.4 g, 20 M), Man-1-P (about 1.5 g, about 50 mM), PEP (1.0 g, 42.7 HM), GDP (30 mg, 1 mM), dried yeast cells (0.4 g), pyruvate kinase PK (300 U), recombinant α1,2-ManT (1.2 U) and inorganic pyrophosphatase (2 U) was slightly stirred at room temperature for 72 hours, then centrifuged. The supernatant was lyophilized and extracted with methanol. After removal of the methanol, the product was purified by silica gel column chromatography (CHCl :CH3OH:H2O=6: 3:0.5, v/v/v) to afford Manα1, 2ManαOMe (Compound 3) (96 mg) in 38 percent overall yield based on consumed α-methyl-D-mannopyranoside. 1H NMR (D2O) δ3.41 (s, 3H), 3.60-3.80 (m, 6H), 3.86 (dd, 1H, J=3.5, 10 Hz), 3.88 (dd, 1H, J=3.5, 10 Hz), 3.90 (d, 1H, d, J=1.5 Hz), 3.92 (d, 1H, J=l Hz), 3.97 (dd, 1H, J=2, 3.5 Hz), 4.08 (dd, 2H, J=2, 3.5 Hz), 5.02 (d, 1H, d, J=2 Hz), 5 .04 (d, 1H, J=2.0 Hz). 13C {1H} NMR (D2O) δ54.90, 61.01, 61.24, 66.98, 67.03, 70.02, 70.29, 70.37, 72.63, 73.40, 78.62, 99.40, 102.43. HRMS calculated for C13H24O11Na+ (M+Na+) 379.1216, found 379.1220. dried yeast cells (0.4 g), pyruvate kinase PK (300 U), recombinant α1,2-ManT (1.2 U) and inorganic pyrophosphatase (2 U) extracted with methanol After removal of the methanol the product was purified by silica gel column chromatography (CHCl

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: α-mannose phenylaminocyclobutenedione (250 mg; 0.37 mmol) was dissolved in a mixture of Ethanol/H2O (3/2) (10 mL) and triethyamine (400 μL) was added dropwise to the solution of APTS (Aminopropyltriethoxysilane) grafted nanoparticles DB060 (250 mg in 10 ml of EtOH). The mixture was stirred during 16 h. The nanoparticles were then centrifugated and washed with water and ethanol and dried under vacuum to afford 232 mg of grafted nanoparticles. The concentration of α-mannose phenylaminocyclobutenedione grafted on the surface of the DB103 nanoaprticle is 0.089 mmol/g. washed with water and ethanol dried under vacuum to afford 232 mg of grafted nanoparticles

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nanoparticles DB052 (200 mg) were stirred up by ultrasounds for 30 minutes in ethanol (5 mL). α-mannose phenylaminocyclobutenedione derivatives (71 mg, 1.8 10−4 mol, structure here above) was dissolved in an ethanol/water mixture (10 ml, 3/2). The α-mannose phenylaminocyclobutenedione derivative solution was added dropwisely to the nanoparticle suspension. Triethylamine (500 μL) was added, and the suspension was stirred for 18 hours. After centrifugation, the nanoparticles were dispersed in water and centrifuged (3 cycles), then dispersed in ethanol and centrifugated (two cycles). Functionalized nanoparticles (DB069) were obtained (200 mg).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nanoparticles DB052 (200 mg) were stirred up by ultrasounds for 30 minutes in ethanol (5 mL). α-mannose phenylaminocyclobutenedione derivatives (71 mg, 1.8 10−4 mol, structure here above) was dissolved in an ethanol/water mixture (10 ml, 3/2). The α-mannose phenylaminocyclobutenedione derivative solution was added dropwisely to the nanoparticle suspension. Triethylamine (500 μL) was added, and the suspension was stirred for 18 hours. After centrifugation, the nanoparticles were dispersed in water and centrifuged (3 cycles), then dispersed in ethanol and centrifugated (two cycles). Functionalized nanoparticles (DB069) were obtained (200 mg).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: α-D-mannopyranose; β-D-mannopyranose; α-D-mannofuranose; β-D-mannofuranose; L-mannose; α-L-mannopyranose; β-L-mannopyranose; α-L-mannofuranose; β-L-mannofuranose

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction mixture (100 mL, 100 mM Tris, pH 7.5, 10 mM MgCl2, 10 mM MnCl2, 5 mM EDTA, 5 ThM NaN3, 1 mm ATPe 0.01 mM theophylline and 0.03 mM 2, 3-dimercaptopropanol) containing α-methyl-D-mannopyranoside (0.4 g, 20 M), Man-1-P (about 1.5 g, about 50 mM), PEP (1.0 g, 42.7 HM), GDP (30 mg, 1 mM), dried yeast cells (0.4 g), pyruvate kinase PK (300 U), recombinant α1,2-ManT (1.2 U) and inorganic pyrophosphatase (2 U) was slightly stirred at room temperature for 72 hours, then centrifuged. The supernatant was lyophilized and extracted with methanol. After removal of the methanol, the product was purified by silica gel column chromatography (CHCl :CH3OH:H2O=6: 3:0.5, v/v/v) to afford Manα1, 2ManαOMe (Compound 3) (96 mg) in 38 percent overall yield based on consumed α-methyl-D-mannopyranoside. 1H NMR (D2O) δ3.41 (s, 3H), 3.60-3.80 (m, 6H), 3.86 (dd, 1H, J=3.5, 10 Hz), 3.88 (dd, 1H, J=3.5, 10 Hz), 3.90 (d, 1H, d, J=1.5 Hz), 3.92 (d, 1H, J=l Hz), 3.97 (dd, 1H, J=2, 3.5 Hz), 4.08 (dd, 2H, J=2, 3.5 Hz), 5.02 (d, 1H, d, J=2 Hz), 5 .04 (d, 1H, J=2.0 Hz). 13C {1H} NMR (D2O) δ54.90, 61.01, 61.24, 66.98, 67.03, 70.02, 70.29, 70.37, 72.63, 73.40, 78.62, 99.40, 102.43. HRMS calculated for C13H24O11Na+ (M+Na+) 379.1216, found 379.1220. dried yeast cells (0.4 g), pyruvate kinase PK (300 U), recombinant α1,2-ManT (1.2 U) and inorganic pyrophosphatase (2 U) extracted with methanol After removal of the methanol the product was purified by silica gel column chromatography (CHCl