Total Synthesis of Teixobactin
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Open Access
Type
ArticleAuthor/s
Giltrap, Andrew M.Dowman, Luke J.
Nagalingam, Gayathri
Ochoa, Jessica L.
Linington, Roger G.
Britton, Warwick J.
Payne, Richard J.
Abstract
The first total synthesis of the cyclic depsipeptide natural product teixobactin is described. Synthesis was achieved by solid-phase peptide synthesis, incorporating the unusual l-allo-enduracididine as a suitably protected synthetic cassette and employing a key on-resin esterification and solution-phase macrolactamization. The synthetic natural product was shown to possess potent antibacterial activity against a range of Gram-positive pathogenic bacteria, including a virulent strain of Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus (MRSA).The first total synthesis of the cyclic depsipeptide natural product teixobactin is described. Synthesis was achieved by solid-phase peptide synthesis, incorporating the unusual l-allo-enduracididine as a suitably protected synthetic cassette and employing a key on-resin esterification and solution-phase macrolactamization. The synthetic natural product was shown to possess potent antibacterial activity against a range of Gram-positive pathogenic bacteria, including a virulent strain of Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus (MRSA).
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Date
2016-05-18Publisher
American Chemical SocietyFunding information
ARC FT130100150Licence
OtherFaculty/School
Faculty of ScienceShare