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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...

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

Acid-Catalyzed Hydration of Alkenes

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

Base-Catalyzed Aldol Addition Reaction

Base-Catalyzed Aldol Addition Reaction

As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.

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Updated: Jan 23, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Peptide Cyclization Catalyzed by Cyanobactin Macrocyclases.

Wael E Houssen^1,2,3

¹Marine Biodiscovery Centre, Chemistry Department, University of Aberdeen, Aberdeen, UK.

Methods in Molecular Biology (Clifton, N.J.)

|June 5, 2019

Summary

This study details using cyanobacterial macrocyclases for efficient cyclic peptide synthesis. It provides practical methods for enzyme expression, purification, and in vitro reactions, aiding therapeutic development.

Keywords:

Cyanobactins Cyclic peptides Macrocyclases Patellamides RiPPs Ribosomal peptides

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Area of Science:

Biochemistry
Medicinal Chemistry
Synthetic Biology

Background:

Cyclic peptides are a promising therapeutic class targeting challenging biological interactions.
Traditional N-to-C peptide macrocyclization is chemically difficult and low-yielding.

Purpose of the Study:

To provide practical guidance on using cyanobacterial macrocyclases for peptide synthesis.
To detail heterologous expression, purification, and in vitro enzymatic reactions.
To discuss product recovery from enzymatic reaction mixtures.

Main Methods:

Heterologous expression of macrocyclase enzymes.
Enzyme purification techniques.
In vitro biochemical assays for macrocyclization.
Product isolation and purification strategies.

Main Results:

Established protocols for macrocyclase production and purification.
Demonstrated feasibility of in vitro enzymatic macrocyclization.
Outlined methods for recovering cyclic peptide products.

Conclusions:

Cyanobacterial macrocyclases offer a viable enzymatic solution for challenging peptide macrocyclization.
This work provides a practical framework for researchers developing cyclic peptide therapeutics.