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Preparation and Reactions of Sulfides

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Solid-Phase-Based Synthesis of Lactazole-Like Thiopeptides.

Yue Zhang¹, Alexander A Vinogradov¹, Jun Shi Chang¹

¹Department of Chemistry, Graduate School of Science, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.

Organic Letters

|October 25, 2022

Summary

This summary is machine-generated.

Researchers developed a new method for synthesizing lactazole-like thiopeptides, crucial for developing TNIK-inhibitor drugs. This scalable approach enables the creation of diverse thiopeptide compounds for biological research and drug discovery.

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Area of Science:

Medicinal Chemistry
Organic Synthesis
Drug Discovery

Background:

Thiopeptides are a class of natural products with diverse biological activities.
Developing efficient synthetic routes for novel thiopeptide analogs is crucial for drug discovery.
Lactazole-like thiopeptides represent a promising area for therapeutic intervention.

Purpose of the Study:

To report a novel synthetic strategy for de novo discovered lactazole-like thiopeptides.
To enable the modular assembly of peptide chains using a central triheterocyclic amino acid.
To develop a method for preparing C-terminally functionalized thiopeptides for biological evaluation.

Main Methods:

Convergent and scalable preparation of a key triheterocyclic amino acid.
Fmoc solid-phase peptide synthesis for modular peptide chain assembly.
Development of a technique for C-terminal functionalization of thiopeptides.

Main Results:

Successful synthesis of 11 TNIK-inhibitor thiopeptides.
Synthesis of 6 derivatives of these thiopeptides.
Demonstration of multimilligram scale synthesis, highlighting practical utility.

Conclusions:

The developed synthetic strategy is efficient and scalable for lactazole-like thiopeptides.
The methodology facilitates modular assembly and C-terminal functionalization.
The protocols are suitable for producing compounds for biological studies and potential therapeutic development.