反应详情

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).

1. customThe solvent was removed in vacuo
2. dissolutionthe residue was redissolved in acetonitrile/water (1:1)
3. filtrationfiltered
4. custompurified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35)
5. customThe relevant fractions were collected
6. concentrationconcentrated in vacuo
7. stirringstirred at room temperature overnight
8. customThe solvent is removed in vacuo
9. dissolutionthe residue redissolved in chloroform/methanol (95:5)
10. filtrationfiltered
11. custompurified by straight phase chromatography on a CHROMATOTRON
12. customThe relevant fractions are collected
13. concentrationconcentrated in vacuo
14. customThe protecting groups of the α-ε amino groups are removed by standard reactions
15. customBoc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes
16. customThe solvent is removed in vacuo
17. customFmoc is removed
18. additionby treating the residue with 20% piperidine in dimethylformamide for 30 minutes
19. customthe solvent is removed in vacuo
20. customThe final product is purified by reversed phase chromatography (Lobar RPSB)