Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 8, Pages 2681-2685Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo035712x
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A simple and efficient preparation of gramicidin S and its analogues is described. It involves solid-phase peptide synthesis and on-resin macrolactamization without side chain protection, affording cyclic products in high yield and high purity. The high specificity of the cyclization reaction was shown to originate in the formation of a pre-organized conformation of the linear biosynthetic precursor of gramicidin S. This facile method will provide convenient access to the analogues of the natural product for functional optimization to counter microbial resistance.
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