Synthesis and hydrogen bonding capabilities of biphenyl-based amino acids designed to nucleate β-sheet structure

CL Nesloney, JW Kelly

Index: Nesloney, Carey L.; Kelly, Jeffery W. Journal of Organic Chemistry, 1996 , vol. 61, # 9 p. 3127 - 3137

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Citation Number: 20

Abstract

The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'- biphenylcarboxylic acid (2) are described. These residues were designed to nucleate β- sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i+ 1 and i+ 2 residues of the β-turn. N-Benzyl-3'-(2- (benzylamido) ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'- ...