Solid-phase synthesis of coralmycin A/epi-coralmycin A and desmethoxycoralmycin A.
Org Biomol Chem
; 19(28): 6291-6300, 2021 07 21.
Article
em En
| MEDLINE
| ID: mdl-34212970
ABSTRACT
The total synthesis of the natural product coralmycin A/epi-coralmycin A, as well as a desmethoxy analogue is described. Synthesis was achieved via a divergent, bidirectional solid-phase strategy, including a key on-resin O-acylation, O to N acyl shift, and O-alkylation protocol to incorporate the unusual 4-amino-2-hydroxy-3-isopropoxybenzoic acid motifs. The synthetic natural product was generated as a 1 1 mixture of epimers at the central ß-methoxyasparagine residue and exhibited potent antibacterial activity against a panel of ten Gram-negative and seven Gram-positive organisms. The desmethoxy analogue possessed significantly more potent antimicrobial activity against this panel with minimal inhibitory concentrations (MICs) as low as 50 nM.
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Base de dados:
MEDLINE
Assunto principal:
Depsipeptídeos
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article