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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.9K
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...
2.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.5K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
2.5K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.0K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.0K

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Related Experiment Video

Updated: Jul 18, 2025

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
06:17

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis

Published on: November 22, 2024

472

Morpholine, a strong contender for Fmoc removal in solid-phase peptide synthesis.

Sinenhlanhla N Mthembu1,2, Amit Chakraborty1, Ralph Schönleber3

  • 1Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|August 23, 2023
PubMed
Summary

Morpholine offers a greener alternative for Fmoc removal in solid-phase peptide synthesis (SPPS). It efficiently removes Fmoc, minimizing side reactions and yielding high-purity peptides like somatostatin.

Keywords:
Fmocaspartimidediketopiperazineside reactionssolid-phase peptide synthesis

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Area of Science:

  • Organic Chemistry
  • Peptide Synthesis
  • Green Chemistry

Background:

  • Solid-phase peptide synthesis (SPPS) commonly uses piperidine for Fmoc removal.
  • Piperidine use can lead to side reactions like diketopiperazine and aspartimide formation.
  • There is a need for greener and safer reagents in SPPS.

Purpose of the Study:

  • To evaluate morpholine as a greener alternative to piperidine for Fmoc removal in SPPS.
  • To assess the efficiency and selectivity of morpholine in Fmoc deprotection.
  • To compare the purity of peptides synthesized using morpholine versus piperidine.

Main Methods:

  • Fmoc removal using 50%-60% morpholine in dimethylformamide (DMF).
  • Synthesis of somatostatin as a model peptide.
  • Analysis of peptide purity and side-product formation.

Main Results:

  • Morpholine efficiently removed Fmoc in SPPS.
  • Morpholine minimized diketopiperazine and aspartimide formation.
  • Somatostatin synthesized with morpholine showed comparable purity to that synthesized with piperidine.

Conclusions:

  • Morpholine is a viable and greener alternative for Fmoc removal in SPPS.
  • Morpholine-based Fmoc removal offers improved selectivity and reduced side reactions.
  • This method supports the development of more sustainable peptide synthesis protocols.