Accessing the disallowed conformations of peptides employing amide-to-imidate modification |
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Authors: | Reddy Damodara N Thirupathi Ravula Prabhakaran Erode N |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, CV Raman Avenue, Bangalore, India 560012. |
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Abstract: | Selective modification of the C-terminal amide in peptides to dihydrooxazine (a novel stable imidate isostere) by intramolecular nucleophilic cyclo-O-alkylation of the corresponding N-(3-bromopropyl)amides results in constraining of the C-terminal residue in natively disallowed conformations both in crystals and in solution. |
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