Influence of steric effects in solid-phase aza-peptide synthesis |
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Authors: | Meeli Arujõe Anu Ploom Anton Mastitski Jaak Järv |
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Institution: | Institute of Chemistry, University of Tartu, 14A Ravila Str, Estonia |
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Abstract: | Aza-peptides are peptide analogs with potential applications as drug candidates. However, due to difficulties associated with the synthesis of these compounds, information regarding their bioactivity is very limited. Herein, we identify steric hindrance as one reason for the slowness of the aza-peptide bond formation reaction. The steric effect of the side group of amino acids in their coupling with the semicarbazide moiety in the synthesis of a model peptide, H-AA-AzAla-Phe-NH2, was studied and quantified using COMU as a coupling reagent. Characterization of the role of this structural factor in aza-peptide bond synthesis is essential for outlining a new and efficient synthesis protocol. |
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Keywords: | Aza-peptide COMU Kinetics Steric effect SPPS |
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