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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...

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...

Esters to β-Ketoesters: Claisen Condensation Mechanism

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.

Types of Step-Growth Polymers: Polyesters

Types of Step-Growth Polymers: Polyesters

The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the...

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Updated: Jun 26, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Squaric esters as peptide stapling reagents.

Adam X Wayment¹, Nye C Johnson¹, Mariur Rodriguez Moreno¹

¹Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA.

Tetrahedron Letters

|May 13, 2024

Summary

This summary is machine-generated.

Squaric esters enable selective peptide stapling via amide bond formation. This method creates stable, helical peptides, offering a new tool for peptide modification and drug design.

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Last Updated: Jun 26, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Published on: September 28, 2022

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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

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

Published on: February 6, 2020

Area of Science:

Organic Chemistry
Medicinal Chemistry
Biochemistry

Background:

Peptide stapling is crucial for stabilizing peptide secondary structures.
Developing efficient and selective methods for peptide stapling is an ongoing challenge.

Purpose of the Study:

To introduce squaric esters as novel bifunctional reagents for peptide stapling.
To demonstrate the versatility and stability of squaric amide staples.

Main Methods:

Utilized squaric esters for selective reactions with amine-containing side chains on peptides.
Performed peptide stapling on solid-phase synthesis platforms.
Analyzed stapled peptide structure and stability using circular dichroism and acid-cleavage tests.

Main Results:

Squaric esters effectively formed stable squaric amide staples under mild conditions.
Peptide stapling occurred at various positions with diverse amine linkers (e.g., Lysine, ornithine).
Stapled peptides exhibited enhanced helicity and stability against strong acid treatment.

Conclusions:

Squaric esters are efficient bifunctional reagents for selective peptide stapling.
The resulting squaric amide staples enhance peptide helicity and structural stability.
This methodology provides a valuable approach for peptide engineering and therapeutic development.