Journal
ORGANIC LETTERS
Volume 21, Issue 7, Pages 2095-2100Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00378
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- Netherlands Organization for Scientific Research (NWO-TTW) [12557]
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In Nature, multicyclic peptides constitute a versatile molecule class with various biological functions. For their pharmaceutical exploitation, chemical methodologies that enable selective consecutive macrocyclizations are required. We disclose a combination of enzymatic macrocyclization, CLIPS alkylation, and oxime ligation to prepare tetracyclic peptides. Five new small molecular scaffolds and differently sized model peptides featuring noncanonical amino acids were synthesized. Enzymatic macrocyclization, followed by one-pot scaffold-assisted cyclizations, yielded 21 tetracyclic peptides in a facile and robust manner.
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