期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 60, 页码 15046-15049出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704277
关键词
biofilms; cyclic peptides; natural products; peptides; solid-phase synthesis
资金
- Australian Postgraduate Award
- John A. Lamberton Scholarship
- ARC Future Fellowship [FT130100150]
- NSERC [RGPIN-2016-03962]
The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare -OH-glycine functionality. Herein the first total synthesis of skyllamycinsA-C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and an N-terminal glyoxylamide moiety served as a key transformation to install the unique -OH-glycine unit and generate the natural products in the final step of the synthesis.
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