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URL : https://hal.archives-ouvertes.fr/hal-01073781
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, solution of 3 8 (160 mg, 0.117 mmol) and 4 9 (126 mg, 0.141 mmol, 1.2eq) in dry CH2Cl2 with molecular sieves was stirred at room temperature for 1h. To this mixture, TMSOTf (3 µL, 0.017 mmol, 15 %) was added and stirred until TLC showed complete conversion of the starting material (1 h). The reaction was quenched by adding triethylamine (20 µL), filtered through a plug of Celite® and the filtrate was concentrated. The crude was purified by flash chromatography obtaining 5 (185 mg, 76%), The emerging role of native mass spectrometry in characterizing the structure and dynamics of macromolecular complexes, vol.24, pp.1176-1192, 2015.
, 10.5 (c=0.5. CHCl3); 1 H NMR (500 MHz, CDCl3) ? 7.92-7.61 (m, 12H, Ar), vol.7, p.54
, (m, 2H, H-6bC, H-6aA), 3.39 (dd, J = 11.0, 3.8 Hz, 1H, H-6bA, m, 1H, H-5E), 2.04 (s, 3H, CH3 Ac), 2.03 (s, 3H, CH3 Ac), 1.99 (s, 3H, CH3 Ac), 1.97 (s, 3H, CH3 Ac), 1.87 (s, 3H, CH3 Ac), 1.85 (s, 3H, CH3 Ac), 1.42-1.22 (m, 4H, CH2, vol.1
, +0.9, p.500
, MHz, CDCl3) ? 7.95-7.47 (m, 12H, Ar), 7.34-7.20 (m, 9H, Ar), 7.20-7.11 (m, 1H, Ar), 7.03-6.92 (m, 7H, Ar)
, 2x CH2 Bn), 4.59 (d, J = 12.1 Hz, 1H, CH2 Bn
, Tetrahedron Asymmetry, vol.20, pp.851-856, 2009.
, Chem. Eur. J, vol.14, pp.1304-1311, 2007.
, mmol) and 4 2 (80 mg, 0.092 mmol, 1.3 eq) in dry CH2Cl2 (14 mL) with molecular sieves was stirred at room temperature for 1h. The mixture was cooled down to-40°C, TMSOTf (2 µL, 15%) was added and stirred at this temperature until TLC showed complete conversion of the starting material (1 h). The reaction was quenched by adding triethylamine (5 µL), vol.6598, 2003.
, 1?4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-?-D-glucopyranosyl-(1?4)-2-acetamido3,6-di-O-benzyl-2-deoxy-?-D-glucopyranoside 1. A solution of 7 (32 mg, 11.91 µmol) in n-butanol: ethylene diamine (4:1, 500 µL) was heated at 120°C (3x30 minutes) under microwave irradiation. The mixture was concentrated, co-evaporated with toluene and ethanol and dried under high vacuum overnight. The crude was dissolved in pyridine (1 mL), cooled to 0°C and Ac2O (0.5 mL) and DMAP (1 mg) were added. After overnight reaction at room temperature, the mixture was concentrated and purified by column chromatography in EtOAc:MeOH 95:5, obtaining the crude peracetylated compound. The peracetylated compound is dissolved in MeOH (2 mL) and 0.5M NaOMe in MeOH was added (50 µL, 4.73 (d, J = 12.5 Hz, 1H, CH2 Bn), 4.61 (d, J = 12.1 Hz, 1H, CH2 Bn), 4.54 (s, 1H, H-1C), 4.50-4.25 (m, 10H, 5x, vol.1
, H-6bD, H-6aD', H-6bD', H-6aE, H-6bE, H-6aE', H-6bE, m, 3H, H-5E, CH2N3), 3.193.13 (m, 2H, H-5C, H-5E'), 1.99 (s, 3H, CH3 Ac), 1.98 (s, 3H, CH3 Ac), 1.85 (s, 3H, CH3 Ac, vol.1
, H-2D), 4.03-3.94 (m, 2H, H-4A, H-4B), 3.94-3.37 (m, 40H), 3.20-3.11 (m, 2H, H-5C, H-5E'), 1.99 (s, 3H, CH3 Ac), 1.98 (s, 3H, CH3 Ac), 1.85 (s, 3H, CH3 Ac), 1.83 (s, 3H, CH3 Ac), 1.62-1.52 (m, 4H, 2xCH2 linker), 1.47-1.37 (m, 2H, CH2 linker). 13 C NMR (from HSQC experiment 126MHz, MeOD) ? 128.0, 4-galactosylation of 1: A solution (1.65 mL) of 1 (6.09 mg, 3.41 µmol), uridine 5'-diphospho-?-Dgalactose disodium salt UDP-Gal 20 (179 µL, 3.58 µmol, 1.05 eq), bovine serum albumin BSA (1 mg), bovine milk ?-1,4-galactosyltransferase (100 mU), MnCl2 (2 mM) and Hepes buffer (50mM, pH=7.4) was incubated at 37°C overnight. The resulting mixture was heated at 95°C for 5 min to precipitate the enzyme. After centrifugation, the supernatant was purified by semipreparative HPLC (C18 10x250 mm 5 µm, ammonium formate 20 mM:ACN gradient A) and the collected fractions were evaporated and freeze-dried obtaining 1.53 mg (0.726 µmol, 21%) of compound 10, 1.20 mg (0.613 µmol, 18%) of compound 9, 1.55 mg (0.793 µmol, 23%) of compound 8 and 1.35 mg (0.754 µmol, 22%) of compound 1. 5-azidopentyl ?, vol.8, p.55
, ): m/z: calcd C95H137N7O46Na: 2134.8488 [M+Na] + , found 2134.8472. ?-1,4-galactosylation of 2: A solution (0.5 mL) of 2 (2.13 mg, 1.19 µmol), uridine 5'-diphospho-?-Dgalactose disodium salt UDP-Gal 20 mM (72 µL, 1.44 µmol, 1.21 eq), bovine serum albumin BSA (1 mg), bovine milk ?-1,4-galactosyltransferase(100 mU), MnCl2 (2 mM) and Hepes buffer (50 mM, pH=7.4) was incubated at 37°C for 24h. The resulting mixture was heated at 95 °C for 5 min to precipitate the enzyme. After centrifugation, the supernatant was purified by HPLC (C18 10x100 mm, ACN: H2O 0.1% formic acid, gradient B) and the collected fractions were evaporated and freeze-dried obtaining 720 ?g (0.327 µmol, .10 (m, 1H), 2.05 (s, 3H), 2.03 (s, 3H), 1.78 (s, 3H), 1.78 (s, 3H), 1.61-1.50 (m, 4H), 1.40-1.31 (m, 3H). 13 C NMR (from HSQC experiment 126MHz, MeOD), vol.3, p.3
, HRMS (MALDI): m/z: calcd C102H143N7NaO46: 2224.8958 [M+Na] + , found 2224.8909. ?-1,4-galactosamination of 1: A solution (1 mL) of 1 (5.77 mg, 3.22 µmol), uridine 5'-diphospho-2acetamido-2-deoxy-?-D-galactosamine disodium salt UDP-GalNAc 20mM (178 µL, 3.22 µmol, 1.1 eq), double mutant ?-1,4-galactosyltranferase (400 µL), MnCl2 (10 mM) in Hepes buffer (50mM, pH=7.4) was incubated at 37°C for 44h. The resulting mixture was heated at 95°C for 5 min to precipitate the enzyme. After centrifugation the supernatant was purified by semi-preparative HPLC (ACN:H2O, C18 10x250 mm, 5µm, gradient C). The fractions were concentrated and freeze-dried, obtaining 1.89 mg (0.861 µmol, 26%) of compound 16, 1.67 mg (0.837 µmol, 26 %) of compound 15, 1.48 mg (0.742 µmol, 23%) of compound 14 and 1.118 mg (0.625 µmol, 19%) of compound 1 5-azidopentyl 2, 1.83 (s, 3H, CH3 Ac), 1.82 (s, 3H, CH3 Ac), 1.63-1.52 (m, 4H, 2xCH2 linker), 1.48-1.38 (m, 2H, CH2 linker). 13 C NMR (from HSQC experiment 126MHz, MeOD) ?: 129.1, 128.7, 128.5, 128.5, 128.1, 128.1, 104.7(C-1F, C-1F'), 102.3(C-1A), 101.4(C-1C, C-1E'), vol.101
, 01 (s, 3H, CH3 Ac), 1.99 (s, 3H, CH3 Ac), 1.97 (s, 3H, CH3 Ac), 1.85 (s, 3H, CH3 Ac), 1.83 (s, 3H, 23%) was obtained. 1 H NMR (500 MHz, MeOD) ? 7.43-7.14 (m, 20H, Ph), 5.07 (s, 1H, H-1D), 5.04-4.96 (m, 2H, 2x CH2 Bn, vol.2
, (m, 40H), 3.28-3.22 (m, 4H, CH2N3, H-5B, H-5E), 3.20-3.14 (m, 1H, H-5C), 3.11-3.05 (m, 1H, H-5E'), 2.04 (s, 3H, CH3 Ac), 1.98 (s, 6H, 2x CH3 Ac), 1.83 (s, 6H, 2x CH3 Ac), 1.62-1.53 (m, 4H, After ?-1,4-galactosamination of 1 (5.77 mg, 3.22 µmol) and HPLC purification of the crude using gradient C, 15 (1.668 mg, 0.837 µmol, 26 %) was obtained. 1 H NMR (500 MHz, MeOD) ? 7.45-7.10 (m, 20H, Ph), 5.07 (d, J = 1.5 Hz, 1H, H-1D ), 5.01-4.96 (m, 2H, 2x CH2 Bn, vol.101, p.3
, MnCl2 (20 mM) in MES 80mM buffer pH 6.5 was incubated at room temperature for 48h. The resulting mixture was heated at 95°C for 5 min to precipitate the enzyme. After centrifugation the supernatant was purified by semipreparative HPLC (C18 10x250 mm, 5µm, gradient D, Ammonium formate 20 mM:ACN) and the collected fractions were evaporated and freeze-dried obtaining 1.04 mg of 17 (60%). 1 H NMR (500 MHz, MeOD) ? 7, 1.83 (d, J = 1.4 Hz, 6H 2xCH3 Ac), 1.62-1.51 (m, 4H, 2xCH2), 1.49-1.37 (m, 2H, CH2). 13 C NMR from HSQC experiment (126 MHz, MeOD) ? 127.76, 127.74, 127.68, 127.3, 126.9, vol.4, p.2
, , vol.3, p.3
, mL) of 15 (1.60 mg, 0.803 µmol), guanosine 5?-diphospho-?L-fucose sodium salt GDP-Fucose 20 mM (118.5 µL, 2.35 µmol, 2.9 eq), ?-1,3-fucosyltranferase CeFUT6 (110 µL), MnCl2 (20 mM) in MES 80mM buffer pH 6.5 was incubated at room temperature for 48h. The resulting mixture was heated at 95°C for 5 min to precipitate the enzyme, 16.5. HRMS (MALDI): m/z: calcd C97H140N8NaO45: 2159.8805 [M+Na] + , found 2159.8953. 5-azidopentyl 2-acetamido-2-deoxy-?-D-glucopyranosyl-(1?2)-?-Dmannopyranosyl-(1?3), p.500
, MHz, MeOD) ? 7.43-7.13 (m, 20H, Ph)
, 13 C NMR from HSQC experiment (126 MHz, MeOD)
, After centrifugation, the supernatant was purified by semi-preparative HPLC (C18 10x250 mm 5µm, ammonium formate 20 mM:ACN, gradient E) and the collected fractions were evaporated and freeze-dried obtaining 118 ?g of 21 (0.047 ?mol, 10%), 300 ?g of 19 (0.128 ?mol, 27%) and 44 ?g of 20 (0.018 ?mol 4%) and 0.148 mg (0.674 ?mol, 14%) 5-azidopentyl ?-L-fucopyranosyl-(1?3)-[2-acetamido-2-deoxy-?-D-galactopyranosyl(1?4), 3-fucosylation of 16: A solution (1 mL) of 16 (1.05 mg, 0.476 µmol), guanosine 5?-diphospho-?-L-fucose sodium salt GDP-Fucose 20 mM (51.5 µL, 1.03 µmol, 2.2 eq), ?-1,3-fucosyltranferase CeFUT6 (60 µL), MnCl2 (20 mM) in MES 80mM buffer pH 6.5 was incubated at room temperature for 48h, vol.1
, M+Na] + , found 2362.9724. 5-azidopentyl 2-acetamido-2-deoxy-?-D-galactopyranosyl-(1?4)-2-acetamido-2deoxy-?-D-glucopyranosyl-(1?2)-?-D-mannopyranosyl-(1?3)-{?-L-fucopyranosyl-(1?3)-[2-acetamido2-deoxy-?-D-galactopyranosyl-(1?4)]-2-acetamido-2-deoxy-?-D-glucopyranosyl-(1?2)-?-Dmannopyranosyl-(1?6)}-?-D-mannopyranosyl-(1?4)-2-acetamido-3,6, H NMR (500 MHz, MeOD) ? 7.44-7.13 (m, 20H, Ph), vol.1
, After centrifugation the supernatant was purified by semi-preparative HPLC (ACN:H2O, C18 10x250 mm 5µm, gradient C). The fractions were concentrated and freezed-dried, obtaining 664 ?g (0.284 µmol, 60%) of compound 20. 5-azidopentyl ?-L-fucopyranosyl, A solution (0.5 mL) of 18 (1 mg, 0.468 µmol), uridine 5'-diphospho-2-acetamido-2-deoxy-?-D-galactosamine disodium salt UDP-GalNAc 20mM (35 µL, 0.702 µmol, 1.5 eq), double mutant ?-1,4-galactosyltranferase (50 µL)
, After ?-1,3-fucosylation of 16 (1.05 mg, 0.476 µmol) and HPLC purification of the crude using gradient E, the collected fractions were evaporated and freeze-dried obtaining 0, vol.118
, 500 MHz, MeOD) ? 9.18-8.58 (m, vol.20
, H-1A), 5.84 (d, J = 8.1 Hz, 1H, H-1E'), 5.67 (d, J = 3.1 Hz, 1H, H-2C), 2x CH2 ), 5.95 (d, J = 8.1 Hz, vol.1, p.61
, General hydrogenation procedure: Glycan (0.5-1 mg) is dissolved in 0.5 mL of MeOH containing trifluoroacetic acid (0.1%). The mixture was hydrogenated on a H-Cube hydrogenation apparatus, using 10%Pd/C as catalyst, MeOH containing 0.1%TFA as mobile phase at 2 mL/min, at 30°C and full H2. The collected fraction was concentrated to dryness and purify with SampliQ high performance graphitized carbon cartridges eluting the compound in a mixture of H2O:ACN 8:2. 5-aminopentyl ?-D-galactopyranosyl-(1?4)-2-acetamido-2-deoxy-?-Dglucopyranosyl-(1?2)-?-D-mannopyranosyl-(1?3)-[2-acetamido-2
, HRMS (MALDI): m/z calcd for C61H105N5O41Na: 1586.6177, found 1586.6042. 5-aminopentyl 2-acetamido-2-deoxy-?-D-galactopyranosyl-(1?4)-2-acetamido-2deoxy-?-D-glucopyranosyl-(1?2)-?-D-mannopyranosyl-(1?3)-[2-acetamido-2-deoxy-?-Dglucopyranosyl-(1?2)-?-D-mannopyranosyl-(1?6)]-?-D-mannopyranosyl-(1?4)-2-acetamido-2-deoxy?-D-glucopyranosyl-(1?4)-2-acetamido-2-deoxy-?-D-glucopyranoside 24. The general hydrogenation procedure was applied to 786 ?g (0.39 µmol) of compound 14 and 506 ?g of 24 (80% of yield) were obtained. 1 H NMR (500 MHz, D2O) ? 5.12 (s, 1H), The general hydrogenation procedure was applied to 1.20 mg (0.793 µmol) of 9 and 782 ?g of 24 (81% yield) were obtained. 1 H NMR (500 MHz, D2O) ? 5.12 (s, 1H), 4.93 (s, 1H), 4.64-4.53 (m, 3H), 4.49 (t, J = 8.0 Hz, 2H), 4.25 (d, J = 2.6 Hz, 1H), 4.21-4.17 (m, 1H), 4.11 (dd, J = 3.1, 1.3 Hz, 1H), 4.03-3.40 (m, 47H), 2.99 (t, J = 7.7 Hz, 2H), 2.09 (s, 3H), 2.06 (s, 3H), 2.05 (s, 3H), 2.03 (s, 3H), 1.72-1.63 (m, 2H), 1.63-1.55 (m, 2H), 1.45-1.34 (m, 2H). 13 C NMR from HSQC experiment (126 MHz, D2O) ? 102.9, vol.2
, (1?4)-2-acetamido-2-deoxy-?-D-glucopyranosyl-(1?4)2-acetamido-2-deoxy-?-D-glucopyranoside 29. The general hydrogenation procedure was applied to 810 ?g, Hz, 2H), 2.10 (s, 3H), 2.09 (s, 3H), 2.05 (d, J = 1.6 Hz, 9H), vol.2
, 10 (s, 3H), 2.08 (s, 3H), 2.06 (s, 6H), 2.05 (s, 3H), 2.04 (s, 3H), 1.72-1.64 (m, 2H), 1.64-1.56 (m, 2H), 1.45-1.37 (m, 2H), 1.28 (d, J = 6.4 Hz, 3H). 13 C NMR from HSQC experimente ? 101, m, 5H), 3.00 (t, J = 7.6 Hz, 2H, vol.2, p.1, 2016.
, C-type lectins receptor (CLR) arrays to screen immunocompatibility and reactivity of biological sample, 2016.
, C-type lectins receptor (CLR) arrays to screen immunocompatibility and reactivity of biological sample, IBS day, 2016.
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, TETRALEC, Artificial Tetrameric Lectins, a tool for multivalency enhancement