1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(2',6'-Diaminohexanoylamino)-3,4,5-Trihydroxytetra-Hydropyran-2-ylmethyl 10,12-Tricosadiynoate

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Reaction Steps

1-Amino-1-deoxy-β-D-galactose (180 mg, 1 mmol), and Fmoc-Lys(Boc)-OPfp (650 mg, 1 mmol) were dissolved in 4 ml dry dimethylformamide and stirred at room temperature overnight. The solvent was removed in vacuo, the residue was redissolved in acetonitrile/water (1:1), filtered and purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35). The relevant fractions were collected, concentrated in vacuo, and the product was characterised by NMR. The purified product (1 g, 1 mmol), 10,12-tricosadiynoic acid (350 mg, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide are dissolved in 10 ml dry dimethylformamide and stirred at room temperature overnight. The solvent is removed in vacuo, the residue redissolved in chloroform/methanol (95:5), filtered and purified by straight phase chromatography on a CHROMATOTRON. The relevant fractions are collected, concentrated in vacuo, and the product is characterised by NMR. The protecting groups of the α-ε amino groups are removed by standard reactions. Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes. The solvent is removed in vacuo. Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes, and the solvent is removed in vacuo. The final product is purified by reversed phase chromatography (Lobar RPSB).

Provenance & Evidence