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Total Synthesis of Mannopeptimycin β via β-Hydroxyenduracididine Ligation

2021; American Chemical Society; Volume: 143; Issue: 32 Linguagem: Inglês

10.1021/jacs.1c05922

1943-2984

Jin‐Zheng Wang, Du’an Lin, Ming Liu, Han Liu, Pilar Blasco, Zhenquan Sun, Yan Chu Cheung, Sheng Chen, Xuechen Li,

Chemical Synthesis and Analysis

Nonribosomal peptide synthesis in bacteria has endowed cyclic peptides with fascinating structural complexity via incorporating nonproteinogenic amino acids. These bioactive cyclic peptides provide interesting structural motifs for exploring total synthesis and medicinal chemistry studies. Cyclic glycopeptide mannopeptimycins exhibit antibacterial activity against antibiotic-resistant Gram-positive pathogens and act as the lipid II binder to stop bacterial cell wall biosynthesis. Here, we report a strategy streamlining solution phase–solid phase synthesis and chemical ligation-mediated peptide cyclization for the total synthesis of mannopeptimycin β.