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Avoiding Undesired Intramolecular Diketopiperazine Formation during Peptoid Chain Elongation Using a Microflow

Yuki Okura1, Yuma Tanaka1, Shinichiro Fuse1

  • 1Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya 464-8601, Japan.

Organic Letters
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Summary

This study introduces a microflow reactor to prevent unwanted side reactions in peptoid synthesis. This method efficiently produces peptoids with superior productivity and lower cost compared to traditional techniques.

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Area of Science:

  • Synthetic Organic Chemistry
  • Chemical Engineering
  • Materials Science

Background:

  • Intramolecular reactions pose a significant challenge in synthetic organic chemistry, often hindering desired intermolecular reactions.
  • Diketopiperazine formation is a common undesired intramolecular side reaction during peptide and peptoid synthesis.

Purpose of the Study:

  • To develop a microflow reactor system for synthesizing peptoids.
  • To prevent undesired intramolecular diketopiperazine formation during N-alkylation in peptoid synthesis.
  • To demonstrate the efficiency and cost-effectiveness of the microflow approach compared to conventional methods.

Main Methods:

  • Utilized a microflow reactor for N-alkylation reactions in peptoid synthesis.
  • Optimized reaction conditions within the microflow system to suppress intramolecular side reactions.
  • Scaled up the synthesis of a cyclic peptoid on a gram scale using the developed microflow approach.

Main Results:

  • Successfully avoided undesired intramolecular diketopiperazine formation during N-alkylation.
  • Synthesized fifteen peptoids in good to high yields.
  • Achieved gram-scale synthesis of a cyclic peptoid with the microflow method.

Conclusions:

  • The microflow reactor approach effectively prevents intramolecular side reactions in peptoid synthesis.
  • This method offers significantly superior productivity and cost-effectiveness over traditional solid-phase synthesis.
  • The developed microflow system is a viable and efficient alternative for peptoid synthesis.