Synthesis and conformational features of topographically constrained designer chimeric amino acids: The β-isopropyl phenylalanines

S Liao, MD Shenderovich, J Lin, VJ Hruby

Index: Liao, Subo; Shenderovich, Mark D.; Lin, Jun; Hruby, Victor J. Tetrahedron, 1997 , vol. 53, # 49 p. 16645 - 16662

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Citation Number: 25

Abstract

All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, β-isopropylphenylalanine or β-phenylleucine, were asymmetrically synthesized in five to six steps in 20–25% overall yield. Computer-assisted molecular modeling revealed that the β-isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations.