A new method for gamma-acylation of protected glutamic acids, involving intramolecular rearrangement of an acyl urethane, has been devised to prepare the protected gamma-carboxyglutamates 7, 9 and 11 and the protected 4-acylglutamates 15 and 22 from N,N-bisurethanes or N-acyl-N-urethanes of general structure 1. When the formyl-urethane 17 was used in the reaction, then the intermediate 18 in the intramolecular rearrangement was obtained.
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http://dx.doi.org/10.1039/b503900b | DOI Listing |
J Biol Chem
June 2012
Departments of Biology, University of Utah, Salt Lake City, Utah 84112, USA.
Conantokins are short peptides derived from the venoms of marine cone snails that act as antagonists of the N-methyl-D-aspartate (NMDA) receptor family of excitatory glutamate receptors. These peptides contain γ-carboxyglutamic acid residues typically spaced at i,i+4 and/or i,i+7 intervals, which by chelating divalent cations induce and stabilize helical conformation of the peptide. Introduction of a dicarba bridge (or a staple) can covalently stabilize peptide helicity and improve its pharmacological properties.
View Article and Find Full Text PDFOrg Biomol Chem
June 2005
Department of Chemistry, University of Sussex, Falmer, Brighton, UKBN1 9QJ.
A new method for gamma-acylation of protected glutamic acids, involving intramolecular rearrangement of an acyl urethane, has been devised to prepare the protected gamma-carboxyglutamates 7, 9 and 11 and the protected 4-acylglutamates 15 and 22 from N,N-bisurethanes or N-acyl-N-urethanes of general structure 1. When the formyl-urethane 17 was used in the reaction, then the intermediate 18 in the intramolecular rearrangement was obtained.
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