Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia.
Mar Drugs. 2024 Oct 3;22(10):454. doi: 10.3390/md22100454.
The first total synthesis of the Australian marine tunicate fungus-derived cyclic peptide talarolide A () has confirmed the structure previously proposed on the basis of spectroscopic and chemical analyses and re-affirmed the importance of the unique hydroxamate H-bond bridge in ring conformer stabilization. The unexpected co-synthesis of -talarolide A () revealed, for the first time, that hydroxamate H-bond bridging in the talarolide framework invokes non-canonical atropisomerism and that talarolides A (), C (), and D () all exist naturally as atropisomers. These discoveries raise the intriguing prospect that comparable functionalisation of other cyclic peptides, including those with commercial value, could provide ready access to new "unnatural atropisomeric" chemical space, with new and/or improved chemical and biological properties.
澳大利亚海洋被囊动物真菌衍生环肽塔利罗内酯 A 的首次全合成（）证实了先前基于光谱和化学分析提出的结构，并再次确认了独特的羟胺 H 键桥在环构象稳定化中的重要性。-塔利罗内酯 A 的意外共合成（）首次揭示了羟胺 H 键桥在塔利罗内酯骨架中的桥接引起了非经典的对映体异构，并且塔利罗内酯 A（）、C（）和 D（）都以天然的对映异构体形式存在。这些发现提出了一个有趣的前景，即其他环肽的类似官能化，包括那些具有商业价值的环肽，可能会提供更容易进入新的“非天然对映体异构”化学空间的途径，具有新的和/或改进的化学和生物学性质。
