Solid-Phase-Based Synthesis of Lactazole-Like Thiopeptides

Solid-Phase-Based Synthesis of Lactazole-Like Thiopeptides

A strategy for the synthesis of de novo discovered lactazole-like thiopeptides is reported. The approach revolves around a convergent and scalable preparation of the central triheterocyclic amino acid and its utilization in Fmoc solid-phase peptide synthesis for modular peptide chain assembly. A tec...

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Veröffentlicht in:Organic letters 2022-11, Vol.24 (43), p.7894-7899
Hauptverfasser: Zhang, Yue, Vinogradov, Alexander A., Chang, Jun Shi, Goto, Yuki, Suga, Hiroaki
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Sprache:eng
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Amino Acids
Peptides - chemistry
Solid-Phase Synthesis Techniques - methods
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container_end_page 7899
container_issue 43
container_start_page 7894
container_title Organic letters
container_volume 24
creator Zhang, Yue
Vinogradov, Alexander A.
Chang, Jun Shi
Goto, Yuki
Suga, Hiroaki
description A strategy for the synthesis of de novo discovered lactazole-like thiopeptides is reported. The approach revolves around a convergent and scalable preparation of the central triheterocyclic amino acid and its utilization in Fmoc solid-phase peptide synthesis for modular peptide chain assembly. A technique for preparing C-terminally functionalized thiopeptides for biological studies is also described. The syntheses of 11 TNIK-inhibitor thiopeptides and 6 of their derivatives in multimilligram quantities highlight the practical utility of the developed protocols.
doi_str_mv 10.1021/acs.orglett.2c02870
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subjects Amino Acids
Peptides - chemistry
Solid-Phase Synthesis Techniques - methods
title Solid-Phase-Based Synthesis of Lactazole-Like Thiopeptides
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