Short asymmetric synthesis of a model monomeric unit for a/g peptide foldamers based on b -amino linked D-leucine – cis- g -butyrolactone g -acetic acid conjugate

Mohd Tajudin Mohd Ali, Siti Aisyah Aliasak and Allan Patrick G. Macabeo

Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia

Laboratory for Organic Reactivity, Discovery and Synthesis (LORDS), Research Center for the Natural and Applied Sciences, University of Santo Tomas, Espana Blvd., Manila 1015, Philippines

Abstract: This synthetic work reports a concise, asymmetric synthesis of b -amino- g -butyrolactone acetic acid – D-leucine hybrid 1 which will serve as model starting template sub-unit for preparing a/g foldameric oligopeptides containing unnatural g -amino acid residues. The synthesis of cis-substituted 1 was successfully achieved in six linear steps with very good stereoinduction.

Keywords : cis- g -butyrolactone; foldamer; oligopeptide; asymmetric epoxide opening; g -amino acid. © 2017 ACG Publications. All rights reserved.