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Related Experiment Video

Updated: May 19, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

One-pot/sequential native chemical ligation using N-sulfanylethylanilide peptide.

Akira Otaka1, Kohei Sato, Hao Ding

  • 1Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima 770-8505, Japan. aotaka@tokushima-u.ac.jp

Chemical Record (New York, N.Y.)
|August 29, 2012
PubMed
Summary

N-Sulfanylethylanilide (SEAlide) peptides enable efficient synthesis of peptide thioesters. These peptides facilitate native chemical ligation and allow for sequential fragment assembly in protein synthesis.

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Chemical Biology

Background:

  • 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis (SPPS) is a common method for peptide production.
  • Peptide thioesters are crucial intermediates for protein synthesis via native chemical ligation (NCL).
  • Developing facile methods for generating peptide thioesters is essential for advancing protein chemistry.

Purpose of the Study:

  • To develop N-Sulfanylethylanilide (SEAlide) peptides for straightforward synthesis of peptide thioesters.
  • To explore the utility of SEAlide peptides in native chemical ligation (NCL) and protein synthesis.
  • To investigate the tunable reactivity of SEAlide peptides for complex peptide assembly.

Main Methods:

  • Synthesis of SEAlide peptides using Fmoc-based solid-phase peptide synthesis (SPPS).
  • Investigation of SEAlide peptide conversion to thioesters under acidic and phosphate salt conditions.
  • Application of SEAlide peptides in native chemical ligation (NCL) with N-terminal cysteinyl peptides.
  • Demonstration of sequential three- and four-fragment ligation strategies.
  • Achievement of dual-kinetically controlled ligation for simultaneous three-fragment assembly.

Main Results:

  • SEAlide peptides were successfully synthesized and converted to peptide thioesters.
  • The reactivity of SEAlide peptides as thioesters can be modulated by phosphate salts.
  • SEAlide peptides effectively participated in NCL, enabling efficient peptide and protein synthesis.
  • Sequential and one-pot multi-fragment ligation strategies were achieved.
  • Dual-kinetically controlled ligation was successfully demonstrated for the first time using SEAlide peptides.

Conclusions:

  • SEAlide peptides represent a versatile tool for the facile synthesis of peptide thioesters.
  • These peptides significantly advance protein synthesis methodologies, including complex fragment assembly.
  • SEAlide peptides function as effective 'crypto-peptide thioesters' in protein chemistry applications.