FMOC-LYS(BOC)-OPFP

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

Procedure: 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). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo 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 the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RPSB)

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

Procedure: 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). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo 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 the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RPSB)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Commercial N(α)-Fmoc-N(ε)-Boc-L-lysine pentafluorophenyl ester (6.51 mmol) and 4-(nitrooxy)-1-butanol (6.55 mmol) were dissolved in DMF (12 ml) and the mixture was cooled to 0° C. N,N-dimethylaminopyridine (DMAP) (6.55 mmol) were added and the reaction was slowly warmed to room temperature and stirred for 4 hours. Then the mixture was concentrate under reduced pressure and diluted with EtOAc, washed with 5% aqueous Na2HPO4 and brine. the reaction was slowly warmed to room temperature Then the mixture was concentrate under reduced pressure diluted with EtOAc washed with 5% aqueous Na2HPO4 and brine

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

Procedure: 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 RP8B, 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 RP8B). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RP8B, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo 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 the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RP8B)

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

Procedure: 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). The solvent was removed in vacuo the residue was redissolved in acetonitrile/water (1:1) filtered purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35) The relevant fractions were collected concentrated in vacuo stirred at room temperature overnight The solvent is removed in vacuo the residue redissolved in chloroform/methanol (95:5) filtered purified by straight phase chromatography on a CHROMATOTRON The relevant fractions are collected concentrated in vacuo 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 the solvent is removed in vacuo The final product is purified by reversed phase chromatography (Lobar RPSB)