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.

Item Type: Journal Article (Original Article)
Division/Institute: 08 Faculty of Science > Departement of Chemistry and Biochemistry
UniBE Contributor: Bartoloni, Marco; Waltersperger, Sandro; Bumann, Mario; Stocker, Achim; Darbre, Tamis and Reymond, Jean-Louis
Subjects: 500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
ISSN: 1551-7012
Publisher: Michigan Publishing
Language: English
Submitter: Achim Stocker
Date Deposited: 05 Apr 2014 00:28
Last Modified: 07 Jan 2016 08:14
Publisher DOI: 10.3998/ark.5550190.p008.500
Additional Information: Commemorative Issue in Honor of Prof. Pierre Vogel on the occasion of his 70th anniversary
Uncontrolled Keywords: Bicyclic peptides, orthogonality, X-ray crystallography, stereochemistry
BORIS DOI: 10.7892/boris.43779

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