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Design and Synthesis of a Prototype Scaffold for Five‐Residue α‐Helix Mimetics
Author(s) -
Bayly Andrew R.,
White Andrew J. P.,
Spivey Alan C.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300478
Subject(s) - chemistry , scaffold , helix (gastropod) , residue (chemistry) , amide , stereochemistry , octane , selectivity , combinatorial chemistry , biochemistry , organic chemistry , ecology , snail , biology , medicine , biomedical engineering , catalysis
The development of structural mimetics of α‐helices has traditionally focused on representation of the three residues that protrude from one face of the helical surface on three consecutive turns (i.e., i , i +3/ i +4, and i +7). Despite the decisive contribution these residues make to the binding interaction with protein partners, peripheral residues can play important roles particularly with regard to imparting selectivity. Here, we describe the design and synthesis of a model azabicyclo[2.2.2]octane aryl amide scaffold designed to compactly present the i , i +1, i +2, i +4, and i +5 residues of an α‐helix.