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Related Experiment Video

Updated: Feb 12, 2026

Detection of Protein S-Acylation using Acyl-Resin Assisted Capture

Detection of Protein S-Acylation using Acyl-Resin Assisted Capture

Published on: April 10, 2020

Resin-Bound Crypto-Thioester for Native Chemical Ligation.

Naoto Naruse¹, Kento Ohkawachi¹, Tsubasa Inokuma¹

¹Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences , Tokushima University , Tokushima 770-8505 , Japan.

Organic Letters

|April 10, 2018

Summary

Resin-bound N-sulfanylethylanilide (SEAlide) peptides form thioesters without racemization. This unique property enables efficient one-pot peptide ligation, simplifying complex peptide synthesis.

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Area of Science:

Organic Chemistry
Peptide Chemistry
Biochemistry

Background:

Peptide synthesis often involves challenges with racemization and fragment coupling.
Developing efficient ligation strategies is crucial for constructing complex peptides and proteins.

Purpose of the Study:

To investigate the utility of resin-bound N-sulfanylethylanilide (SEAlide) peptides in peptide ligation.
To explore the formation of thioesters and assess potential racemization.
To develop a one-pot ligation strategy using SEAlide peptides.

Main Methods:

Synthesis of resin-bound SEAlide peptides.
Exposure of peptide resin to aqueous solutions with thiols.
Reaction of resin-bound SEAlide peptides with N-terminal cysteinyl peptides.
Analysis of ligation products and assessment of C-terminal amino acid integrity.

Main Results:

Resin-bound SEAlide peptides function as crypto-thioester peptides.
Thioester formation occurs under neutral aqueous conditions without C-terminal amino acid racemization.
Resin-bound SEAlide peptides facilitate ligation with N-terminal cysteinyl peptides, unlike their soluble counterparts.
A one-pot, three-fragment ligation strategy was successfully demonstrated.

Conclusions:

SEAlide peptides, particularly when resin-bound, offer a robust method for thioester formation and peptide ligation.
The distinct reactivity of resin-bound SEAlide peptides enables efficient and racemization-free peptide coupling.
This approach provides a valuable tool for streamlined synthesis of complex peptides.