Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide |
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| Affiliation: | 1. School of Chemistry, The University of New South Wales, UNSW Sydney, NSW 2052, Australia;2. Department of Chemistry, Faculty of Art and Science, Namık Kemal University, Tekirdag, Turkey;3. Department of Chemistry, Faculty of Science, Gebze Technical University, Gebze, Kocaeli, Turkey;1. Office for University-Industry Collaboration, Osaka University, 2-8 Yamada-oka, Suita 565-0871, Japan;2. Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, British Columbia V8W 3V6, Canada;3. Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan;4. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan;1. Institut Pasteur, Department of Structural Biology and Chemistry, Laboratory for Bioorganic Chemistry of Nucleic Acids, CNRS UMR3523, 28, rue du Docteur Roux, 75724 Paris Cedex 15, France;2. UMR 8182, ICMMO, Institut de Chimie Moléculaire et des Matériaux d''Orsay, Université Paris-Sud, Bât 420, 91405 Orsay Cedex, France;3. KU Leuven, Rega Institute for Medical Research, Medicinal Chemistry, Herestraat, 3000 Leuven, Belgium;4. University of Paris Saclay, CNRS, iSSB, UEVE, Genopole, 5 Rue Henri Desbrueres, 91030 Evry, France;1. Department of Biomedical Engineering, Carnegie Mellon University, 5000 Forbes Avenue, Scott Hall 4th Floor, Pittsburgh, PA, 15213, USA;2. Department of Medicine, University of Pittsburgh, Division of Pulmonary, Allergy and Critical Care Medicine, East 1200A Biomedical Science Tower, 200 Lothrop Street, Pittsburgh, PA, 15213, USA;3. Department of Radiology, University of Michigan, 3226A Medical Sciences Building I, 1301 Catherine Street, Ann Arbor, MI, 48109, USA |
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| Abstract: | The synthesis of a bipyridyl amino acid, 2-amino-3-(4′-methyl-2,2′-bipyridin-4-yl) propanoic acid, is described. A short three step synthesis from commercially available 4,4′-dimethyl-2,2′-bipyridine provides the amino acid in 65% enantiomeric excess (ee). An enzyme-mediated chiral resolution increases the ee to 95% in two additional steps. The amino acid was incorporated into a 22 amino acid peptide composed predominantly of alanine. The peptide was found to be 88% α-helical in aqueous solution at 1°C by circular dichroism (CD) spectropolarimetry, indicating a high helical propensity for this amino acid. This amino acid can provide a means to incorporate a metal into structure-forming peptides. |
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