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Related Concept Videos

Preparation of Amides01:29

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 of 1° Amines: Gabriel Synthesis01:28

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...
Peptide Bonds02:43

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...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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 alkylated β-keto acid.

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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets

Published on: November 2, 2011

Solid-phase peptide synthesis using acetonitrile as a solvent in combination with PEG-based resins.

Gerardo A Acosta1, Montserrat del Fresno, Marta Paradis-Bas

  • 1CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, Barcelona Science Park, University of Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|July 28, 2009
PubMed
Summary

Acetonitrile (ACN) effectively couples hindered amino acids in solid-phase peptide synthesis. ACN also serves as a viable alternative to Dimethylformamide (DMF) for various synthesis steps.

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Synthetic Chemistry

Background:

  • Solid-phase peptide synthesis (SPPS) is crucial for generating peptides.
  • Dimethylformamide (DMF) is a common solvent in SPPS but has potential health and environmental concerns.
  • Developing alternative solvents for SPPS is an active area of research.

Purpose of the Study:

  • To evaluate acetonitrile (ACN) as a coupling solvent for hindered amino acids in SPPS.
  • To assess ACN as a DMF alternative for various SPPS steps, including Fmoc removal and washings.

Main Methods:

  • Utilized Fmoc-amino acids and free amino acids anchored on a Benzhydrylamine resin (BAL) synthesis.
  • Performed coupling reactions using ACN as the primary solvent.
  • Evaluated ACN for washing, Fmoc deprotection, and coupling steps in solid-phase peptide synthesis.

Main Results:

  • ACN demonstrated excellent efficiency in coupling sterically hindered Fmoc-amino acids.
  • ACN proved to be a suitable alternative to DMF for essential SPPS operations.
  • Successful peptide synthesis was achieved using ACN, highlighting its versatility.

Conclusions:

  • Acetonitrile is a highly effective solvent for coupling hindered amino acids in SPPS.
  • ACN offers a promising, greener alternative to DMF for multiple SPPS procedures.