Preparative merits of the mixed anhydride (MA) method in the excess use of 
DDZ-amino acids in the peptide synthesis of biologically active new antamanide 
analogues

Birr, Christian; Nassal, Michael; Pipkorn, Rüdiger

doi:10.1111/j.1399-3011.1979.tb01882.x

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Preparative merits of the mixed anhydride (MA) method in the excess use of DDZ-amino acids in the peptide synthesis of biologically active new antamanide analogues

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Birr, Christian
Max Planck Institute for Medical Research, Max Planck Society;

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Nassal, Michael
Max Planck Institute for Medical Research, Max Planck Society;

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Pipkorn, Rüdiger
Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Birr, C., Nassal, M., & Pipkorn, R. (1979). Preparative merits of the mixed anhydride (MA) method in the excess use of DDZ-amino acids in the peptide synthesis of biologically active new antamanide analogues. International journal of peptide and protein research, 13(3), 287-295. doi:10.1111/j.1399-3011.1979.tb01882.x.

Cite as: https://hdl.handle.net/21.11116/0000-0003-933D-3

Abstract

The mixed anhydride (MA) method of peptide synthesis is further simplified by the repetitive excess use of Ddz-amino acids. In six comparative preparations of decapeptides this is demonstrated by the ease and speed of the synthetic manipulations, the efficiency of the monitoring of the reactions and purifications, and by the complete recycling of excess amino acid derivatives. In using of Ddz-amino acyl isobutylformate mixed anhydrides, side reactions are effectively suppressed, as proved by good coupling of Ddz-proline on to prolyl-peptides. Hydrophilic, crystalline and biological active antamanide analogues are obtained containg various functional side groups. The known cis-conformation of the antamanide prolyl-prolyl bonds is also established in the analogues by 13C-n.m.r. measurements. All new compounds are characterized by molecular peaks in the mass spectra.