Positional scanning for peptide secondary structure by systematic solid-phase synthesis of amino lactam peptides

AG Jamieson, N Boutard, K Beauregard…

Index: Jamieson, Andrew G.; Boutard, Nicolas; Beauregard, Kim; Bodas, Mandar S.; Ong, Huy; et al. Journal of the American Chemical Society, 2009 , vol. 131, p. 7917 - 7927

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Citation Number: 52

Abstract

Incorporation of amino lactams into biologically active peptides has been commonly used to restrict conformational mobility, enhance selectivity, and increase potency. A solid-phase method using a Fmoc-protection strategy has been developed for the systematic synthesis of peptides containing configurationally defined α-and β-amino γ-lactams. N-Alkylation of N- silyl peptides with five-and six-member cyclic sulfamidates 9 and 8 minimized bis- ...