Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 1, Pages 259-263Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912095
Keywords
multicomponent reactions; peptides; secondary structures; solid-phase synthesis; beta-sheets
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Funding
- Alexander von Humboldt Foundation
- DAAD
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In contrast to the myriad of methods available to produce alpha-helices and antiparallel beta-sheets in synthetic peptides, just a few are known for the construction of stable, non-cyclic parallel beta-sheets. Herein, we report an efficient on-resin approach for the assembly of parallel beta-sheet peptides in which the N-alkylated turn moiety enhances the stability and gives access to a variety of functionalizations without modifying the parallel strands. The key synthetic step of this strategy is the multicomponent construction of an N-alkylated turn using the Ugi reaction on varied isocyano-resins. This four-component process assembles the orthogonally protected turn fragment and incorporates handles serving for labeling/conjugation purposes or for reducing peptide aggregation. NMR and circular dichroism analyses confirm the better-structured and more stable parallel beta-sheets in the N-alkylated peptides compared to the non-functionalized variants.
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