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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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Industrial insulin production uses genetically engineered E. coli expressing a proinsulin gene controlled by a tryptophan promoter and containing a methionine linker for later cleavage. The cells also carry ampicillin resistance for selective growth. Seed cultures are stored at −80 °C and production begins by thawing a small amount to inoculate starter cultures, which are progressively scaled to a 50,000-L bioreactor. In the bioreactor, E. coli grow in nutrient-rich media under sterile, tightly...

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Related Experiment Video

Updated: May 12, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Polypeptide Preparation by β-Lactone-Mediated Chemical Ligation.

Xinhao Fan^1,2, Yuming Wen², Huan Chen²

¹Department of Chemistry, School of Pharmacy, North Sichuan Medical College, Nanchong, Sichuan 637000, China.

Organic Letters

|June 20, 2024

Summary

A new β-lactone-mediated native chemical ligation (NCL) method enables efficient synthesis of sterically hindered peptides. This epimerization-free approach overcomes limitations of traditional NCL for complex peptide and protein synthesis.

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Area of Science:

Synthetic chemistry
Biochemistry
Peptide synthesis

Background:

Native chemical ligation (NCL) is a key method for synthesizing peptides and proteins.
Traditional NCL struggles with sterically hindered residues and can cause epimerization.
C-terminal thioesters of β-branched amino acids are particularly prone to slow reactions, epimerization, and hydrolysis.

Purpose of the Study:

To develop an epimerization-free NCL method for sterically congested peptide synthesis.
To overcome the limitations of traditional NCL with challenging amino acid residues.

Main Methods:

A novel β-lactone-mediated native chemical ligation strategy was employed.
This method facilitates chemoselective coupling of C-terminal thioester peptides with N-terminal thiol peptides.
The approach was validated for constructing sterically hindered Thr residues and preparing cyclic peptides.

Main Results:

The β-lactone-mediated NCL proceeds rapidly and without detectable epimerization.
The method demonstrates broad side-chain tolerance.
Successfully applied to synthesize challenging cyclic peptides and polypeptidyl thioesters.

Conclusions:

β-lactone-mediated NCL offers an efficient and epimerization-free solution for synthesizing sterically hindered peptides.
This technique expands the scope of NCL for creating complex peptide structures.
Provides a valuable tool for peptide and protein research and development.