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General procedure of amide coupling: To a stirred solution of pent-4-enoyl-XAA acid in THF at 0°C was added triethylamine (1 equiv.), followed by isobutyl chloroformate (1 equiv.) and the mixture vigorously stirred for 5 min and then finally to this was added XA′A′-allyl amide followed by triethylamine (1 equiv.). The reaction mixture was stirred for 5 h at rt and after that the solvent was removed, the residue taken up in ethyl acetate, washed with sodium bicarbonate and saturated citric acid solution and finally with brine. Drying over sodium sulfate, then concentration in vacuo yielded the crude peptide, which was subjected to column chromatography (silica gel, EtOAc:hexane) to afford the desired peptide in good yields.
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General procedure of amide coupling: To a stirred solution of pent-4-enoyl-XAA acid in THF at 0°C was added triethylamine (1 equiv.), followed by isobutyl chloroformate (1 equiv.) and the mixture vigorously stirred for 5 min and then finally to this was added XA′A′-allyl amide followed by triethylamine (1 equiv.). The reaction mixture was stirred for 5 h at rt and after that the solvent was removed, the residue taken up in ethyl acetate, washed with sodium bicarbonate and saturated citric acid solution and finally with brine. Drying over sodium sulfate, then concentration in vacuo yielded the crude peptide, which was subjected to column chromatography (silica gel, EtOAc:hexane) to afford the desired peptide in good yields.
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23
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0344006321
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For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
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For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
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30
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17744399693
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For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
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31
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0011070358
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note
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-1): 3322, 1639, 1542, 1449.
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