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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...

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 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Related Experiment Video

Updated: May 10, 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

Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Ting Wang¹, Samuel J Danishefsky

¹Laboratory of Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center, New York, NY 10065, USA.

Proceedings of the National Academy of Sciences of the United States of America

|July 4, 2013

Summary

This summary is machine-generated.

This study introduces a novel solid-phase peptide synthesis method using thioacids and isonitriles. This approach enables efficient polypeptide chain elongation and fragment coupling for advanced peptide research.

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Area of Science:

Organic Chemistry
Biochemistry
Synthetic Chemistry

Background:

Solid-phase peptide synthesis (SPPS) is a cornerstone of peptide research and drug discovery.
Current SPPS methods face challenges in efficiency and coupling strategies.
Novel chemical methodologies are needed to advance peptide synthesis.

Purpose of the Study:

To describe a new method for solid-phase polypeptide synthesis.
To utilize isonitriles as mediators in peptide bond formation.
To explore applications in reiterative synthesis and fragment coupling.

Main Methods:

Solid-phase synthesis utilizing thioacids as acyl donors.
Reaction mediation via isonitriles to form a thio-formimidate carboxylate mixed anhydride intermediate.
Application of the method for both stepwise elongation and fragment condensation.

Main Results:

Demonstration of isonitrile-mediated polypeptide synthesis on solid phase.
Successful generation of a key reactive intermediate (thio-formimidate carboxylate mixed anhydride).
Validation of the chemistry for reiterative solid-phase peptide synthesis and fragment coupling.

Conclusions:

Isonitrile-mediated chemistry offers a viable alternative for solid-phase peptide synthesis.
The described method provides a new tool for constructing complex peptides.
This approach has potential applications in medicinal chemistry and materials science.