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A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods
Authors:Rani Maharani  Robert TC Brownlee  Andrew B Hughes  Belinda M Abbott
Institution:1. Department of Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria 3086, Australia;2. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor, West Java 45363, Indonesia
Abstract:2S,3S-Hmp]-Aureobasidin L 2 has been successfully synthesised through a combination of solution- and solid-phase peptide synthesis. All of the Fmoc-protected residues including a depsidipeptide, Fmoc-MeVal-Hmp-OH, were prepared in solution phase. Chain elongation on chlorotrityl resin was undertaken using selected coupling reagents including HBTU/HOBt, HATU/HOAt and BTC/collidine. Cleavage of the linear depsinonapeptide was followed by cyclisation to give the desired cyclodepsipeptide.
Keywords:Aureobasidin  N-Methylated cyclodepsipeptide  Depsidipeptide  Fmoc-based solid-phase peptide synthesis
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