Compound 4

Methyl (2-O-sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-sulfonatamido-6-O-sulfonato-α-D-glucopyranosyl)-(1→4)-(2-O-sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-sulfonatamido-6-O-sulfonato-α-D-glucopyranosyl)-(1→4)-(2-O-sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-sulfonatamido-3,6-di-O-sulfonato-α-D-glucopyranosyl)-(1→4)-(2-O-sulfonato-α-L-idopyranosyluronate)-(1→4)-2-deoxy-2-sulfonatamido-6-O-sulfonato-α-D-glucopyranoside heptadecasodium salt

From: Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host–cell interaction

View in PubChem | MDL Molfile | ChemDraw

InChIKey HXTHDLHSFYXKPG-ODHQKSCCSA-A

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A mixture of the O-sulfonated compound 40 (25.2 mg, 7.48 µmol) and 20% Pd(OH)2 on carbon (151 mg) in a mixed solvent of phosphate buffer (20 mM, pH = 7.0) and methanol (1/9 ratio, 4 mL) was equipped with a hydrogen balloon, and the mixture was stirred at room temperature for 2 days. The whole mixture was filtered through celite, and the filtrate was concentrated in vacuo to give a crude amino-alcohol, which was directly used for the next reaction. The amino-alcohol was dissolved in water (2 mL), and the solution was adjusted to pH = 9.5 through the addition of 2 N NaOH(aq). Sulfur trioxide-pyridine complex (95.2 mg, 0.598 mmol) was added to the mixture in four equal portions in half-hour intervals at room temperature, and the pH value was maintained at 9.5 using of 2 N NaOH(aq). After stirring for 3 h, the reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography on Sephadex G-25 using water as eluent. The appropriate fractions were pooled and passed through a column of DOWEX 50WX8-Na+ with water. The product fraction was lyophilized to give the target molecule 4 (13.7 mg, 72%). 1H-NMR (600 MHz, D2O) δ 5.58 (d, J = 3.4 Hz, 1H), 5.54 (d, J = 3.3 Hz, 1H, H-1''), 5.43 (d, J = 3.2 Hz, 1H), 5.31 (d, J = 3.1 Hz, 1H), 5.26 (s, 1H), 5.24 (d, J = 3.3 Hz, 1H), 5.22 (s, 1H), 5.19 (d, J = 4.2 Hz, 1H), 5.15 (s, 1H), 5.08 (s, 2H), 5.05 (d, J = 3.8 Hz, 1H, H-1), 4.50 (d, J = 11.2 Hz, 1H), 4.45-4.42 (m, 1H), 4.40-4.36 (m, 5H, H-3'', H-6a'', H-6b''), 4.35-4.31 (m, 7H, H-6a, H-6b), 4.29-4.27 (m, 1H), 4.24-4.20 (m, 3H), 4.18-4.16 (m, 2H), 4.13 (t, J = 3.9 Hz, 1H, H-5''), 4.06 (s, 1H), 4.01-3.95 (m, 4H, H-5, H-4''), 3.80-3.76 (m, 3H, H-4), 3.72-3.68 (m, 2H, H-3), 3.62 (t, J = 9.8 Hz, 1H), 3.51 (dd, J = 10.1, 3.3 Hz, 1H, H-2''), 3.45 (s, 3H), 3.33-3.29 (m, 3H, H-2, H-2'''', H-2''''''); 13C NMR (150 MHz, D2O) δ 174.2 (C), 172.9 (C), 172.0 (C), 171.7 (C), 99.4 (CH), 99.3 (CH×2), 99.0 (CH), 98.2 (CH), 97.8 (CH), 96.7 (CH), 95.8 (CH), 77.1 (CH), 76.9 (CH), 76.4 (CH), 76.3 (CH), 76.2 (CH), 76.1 (CH), 75.7 (CH), 75.1 (CH), 74.0 (CH), 72.9 (CH), 70.6 (CH), 70.1 (CH), 69.9 (CH), 69.8 (CH), 69.6 (CH), 69.56 (CH), 69.5 (CH), 69.4 (CH), 69.0 (CH), 68.8 (CH), 68.4 (CH), 68.2 (CH), 67.8 (CH), 66.5 (CH2), 66.3 (CH2), 66.1 (CH2), 65.8 (CH2), 57.9 (CH), 57.7 (CH), 57.65 (CH), 56.7 (CH), 55.3 (CH3); HR-ESI-MS (m/z): [M+9Na-12H]3- calcd. for C49H71N4O80S13Na9, 871.5608; found, 871.5614.

Back to article page