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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...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
ATP and Macromolecule Synthesis01:28

ATP and Macromolecule Synthesis

Biological macromolecules are organic compounds, predominantly composed of carbon atoms. The carbon atoms are covalently bonded with hydrogen, oxygen, nitrogen, and other minor elements. There are four major biological macromolecule classes: carbohydrates, lipids, proteins, and nucleic acids.
Most macromolecules are composed of single subunits, or building blocks, called monomers. The monomers combine with each other using covalent bonds to form larger molecules known as polymers.
Conversion of...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Published on: June 20, 2014

Synthesis of cyclic Py-Im polyamide libraries.

Benjamin C Li1, David C Montgomery, James W Puckett

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

The Journal of Organic Chemistry
|October 31, 2012
PubMed
Summary

A new synthesis method enables the creation of cyclic polyamides for DNA binding studies. These compounds show varying cytotoxicity, offering potential for targeted therapies.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Molecular Biology

Background:

  • Cyclic polyamides with GABA turn units show promise for DNA binding.
  • Previous synthetic challenges limited biological studies of these compounds.

Purpose of the Study:

  • To develop a facile modular approach for synthesizing cyclic polyamides.
  • To create a focused library of cyclic polyamides targeting specific DNA elements (ARE and ERE).
  • To evaluate the biological properties, including DNA binding affinity and cytotoxicity, of these novel compounds.

Main Methods:

  • Microwave-assisted solid-phase synthesis of hairpin oligomers followed by macrocyclization.
  • Fmoc protection strategy for selective modifications.
  • DNA thermal denaturation assays for binding affinity measurement.
  • Confocal microscopy for cellular uptake studies.
  • Cytotoxicity assays (IC50 determination).

Main Results:

  • A modular synthesis route yielded cyclic polyamides 1-7 in 12-17% overall yield.
  • Selective modifications on GABA units improved cellular uptake.
  • DNA binding affinities were assessed and compared to hairpin analogs.
  • Variable cytotoxicity was observed across the synthesized compounds.

Conclusions:

  • A practical synthetic strategy for cyclic polyamides has been established.
  • The synthesized compounds demonstrate potential for DNA targeting applications.
  • Further investigation into structure-activity relationships is warranted to optimize therapeutic potential and minimize toxicity.