Stereoselective synthesis and structure determination of a bicyclo[3.3.2]decapeptide

Bartoloni, Marco; Waltersperger, Sandro; Bumann, Mario; Stocker, Achim; Darbre, Tamis; Reymond, Jean-Louis (2014). Stereoselective synthesis and structure determination of a bicyclo[3.3.2]decapeptide. Arkivoc, 2014(3), p. 113. Michigan Publishing 10.3998/ark.5550190.p008.500

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By analogy to the structural diversity of covalent bond networks between atoms within organic molecules, one can design topologically diverse peptides from mathematical graphs by assigning amino acids to graph nodes and peptide bonds to graph edges. The key is to use diamino acids or amino diacids as equivalents of trivalent graph nodes, which enables a variety of graph topologies beyond the standard linear and monocyclic graphs in natural peptides. Here the bicyclic decapeptide A1FGk2VFPE1AG2 (1b) was prepared and crystallized to assign its bridge stereochemistry. The bridge configuration appears as planned by the chirality of the branching amino acids. Bicyclization furthermore depends on the presence of matched chiralities in the branching amino acids. The stereoselective formation of the second bridge opens the way for the synthesis of a large family of bicyclic peptides as promising new scaffolds for drug design.

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