Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

Abstract
Longicatenamides A–D are cyclic hexapeptides isolated from the combined culture of Streptomyces sp. KUSC_F05 and Tsukamurella pulmonis TP-B0596. Because these peptides are not detected in the monoculture broth of the actinomycete, they are key tools for understanding chemical communication in the microbial world. Herein, we report the solid-phase total synthesis and structural confirmation of longicatenamide A. First, commercially unavailable building blocks were chemically synthesized with stereocontrol. Second, the peptide chain was elongated via Fmoc-based solid-phase peptide synthesis. Third, the peptide chain was cyclized in the solution phase, followed by simultaneous cleavage of all protecting groups to afford longicatenamide A. Chromatographic analysis corroborated the chemical structure of longicatenamide A. Furthermore, the antimicrobial activity of synthesized longicatenamide A was confirmed. The developed solid-phase synthesis is expected to facilitate the rapid synthesis of diverse synthetic analogues.

Beilstein J. Org. Chem. 2022, 18, 1560–1566. doi:10.3762/bjoc.18.166

Source: Beilstein Journal of Organic Chemistry - November 18, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: antimicrobial longicatenamides peptidic natural product solid-phase synthesis total synthesis Full Research Paper Source Type: research