Total Synthesis of Skyllamycins
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ArticleAuthor/s
Giltrap, Andrew M.Haeckl, F. P. Jake
Kurita, Kenji L.
Linington, Roger G.
Payne, Richard J.
Abstract
The skyllamycins are a family of highly functionalized non‐ribosomal cyclic depsipeptide natural products which contain the extremely rare α‐OH‐glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of ...
See moreThe skyllamycins are a family of highly functionalized non‐ribosomal cyclic depsipeptide natural products which contain the extremely rare α‐OH‐glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid‐phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C‐terminal amide and an N‐terminal glyoxylamide moiety served as a key transformation to install the unique α‐OH‐glycine unit and generate the natural products in the final step of the synthesis.
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See moreThe skyllamycins are a family of highly functionalized non‐ribosomal cyclic depsipeptide natural products which contain the extremely rare α‐OH‐glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid‐phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C‐terminal amide and an N‐terminal glyoxylamide moiety served as a key transformation to install the unique α‐OH‐glycine unit and generate the natural products in the final step of the synthesis.
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Date
2017-09-14Publisher
WileyLicence
This is the peer reviewed version of the following article: A. M. Giltrap, F. P. J. Haeckl, K. L. Kurita, R. G. Linington, R. J. Payne, Chem. Eur. J. 2017 , 23 , 15046., which has been published in final form at doi.org/10.1002/chem.201704277. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.Share