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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...

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Dehydration Synthesis

Dehydration Synthesis

Overview
Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
Synthesis of carbohydrates
Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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Related Experiment Video

Updated: Jan 9, 2026

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

Peptide Bond Formation through Fragment Condensation with Silylating Reagents.

Kotaro Ishihara¹, Tomohiro Hattori¹, Hisashi Yamamoto¹

¹Peptide Research Center, Chubu University, Kasugai, Aichi 487-8501, Japan.

The Journal of Organic Chemistry

|December 10, 2025

Summary

This study introduces a novel method for peptide bond formation using a specific silylating reagent, minimizing epimerization. This efficient strategy is crucial for synthesizing peptide drugs and complex bioactive molecules.

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Biochemistry

Background:

Peptide bond formation is key in synthesizing peptide drugs.
Liquid-phase peptide synthesis offers efficiency but risks epimerization.
Oxazolone formation during condensation leads to stereocenter epimerization.

Purpose of the Study:

To develop an epimerization-free peptide bond formation method.
To enable efficient synthesis of complex peptides for pharmaceutical applications.
To explore a novel strategy for peptide synthesis in drug development.

Main Methods:

Utilized HSi(OCH(CF3)2)3 as a silylating reagent for peptide coupling.
Applied the method to peptide fragments with diverse functional groups.
Investigated the extent of epimerization during the synthesis process.

Main Results:

Achieved peptide bond formation with minimal epimerization.
Successfully synthesized octapeptides using the developed method.
Demonstrated the reagent's applicability across various peptide structures.

Conclusions:

The novel silylating reagent enables epimerization-free peptide synthesis.
This strategy is suitable for pharmaceutical drug development.
The method shows potential for synthesizing bioactive natural products.