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Peptide Bonds

Peptide Bonds

A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Access to large cyclic peptides by a one-pot two-peptide segment ligation/cyclization process.

Emmanuelle Boll¹, Jean-Philippe Ebran, Hervé Drobecq

¹UMR CNRS 8161, Université de Lille, Pasteur Institute of Lille 59021 Lille, France.

Organic Letters

|December 16, 2014

Summary

A novel N-acetoacetyl protecting group facilitates efficient one-pot synthesis of large cyclic peptides using native chemical ligation and SEA ligation techniques.

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Last Updated: Apr 19, 2026

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Area of Science:

Peptide Chemistry
Organic Synthesis

Background:

Native chemical ligation (NCL) is a powerful method for peptide synthesis.
Challenges remain in synthesizing large cyclic peptides efficiently and mildly.

Purpose of the Study:

To develop an improved method for synthesizing large cyclic peptides.
To utilize a novel protecting group strategy for N-terminal cysteine residues.

Main Methods:

Employing the N-acetoacetyl protecting group for N-terminal cysteine.
Implementing a one-pot native chemical ligation/SEA ligation sequence.

Main Results:

Achieved efficient and mild synthesis of large cyclic peptides.
Demonstrated the utility of the N-acetoacetyl protecting group in ligation strategies.

Conclusions:

The N-acetoacetyl protecting group enables a streamlined approach to cyclic peptide synthesis.
This method provides access to complex cyclic peptide structures with high efficiency.