Open AccessTotal Synthesis of Teixobactin
Author(s) -
Andrew M. Giltrap,
Luke J. Dowman,
Gayathri Nagalingam,
Jessica L. Ochoa,
Roger G. Linington,
Warwick J. Britton,
Richard J. Payne
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b01324
Subject(s) - chemistry , depsipeptide , natural product , staphylococcus aureus , mycobacterium tuberculosis , total synthesis , antibacterial activity , bacteria , virulence , peptide , peptide synthesis , combinatorial chemistry , stereochemistry , pathogenic bacteria , microbiology and biotechnology , biochemistry , tuberculosis , biology , medicine , genetics , pathology , gene
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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