Journal
TETRAHEDRON
Volume 65, Issue 11, Pages 2217-2225Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.047
Keywords
Amino acids; Cyclization; Imidazoles; Macrocycles; Peptidomimetics
Categories
Funding
- Deutsche Forschungsgemeinschaft
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Starting from 4-oxa- or 4-azasubstituted 2-amino-3-oxoesters and (S)-valine, chiral imidazole diamino monocarboxylic acids as well as diamino dicarboxylic acids were prepared in a few synthetic steps. Macrolactamization of the side chain protected imidazole amino acids yields the corresponding 18- and 24-membered ring analogues of the naturally occurring cyclic peptide Westiellamide with various anchoring sites. The threefold functionalized scaffolds 2b-4b and the sixfold functionalized scaffold 5 are versatile central modules for artificial receptors and ligands. Structural investigations of threefold functionalized scaffolds based on oxazole and N-methylimidazole units by DFT modeling are provided. (C) 2009 Elsevier Ltd. All rights reserved.
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