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Related Concept Videos

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...
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...
Step-Growth Polymerization: Overview01:03

Step-Growth Polymerization: Overview

Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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...
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael acceptor.
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Solid-phase synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines).

Felix Wojcik1, Simone Mosca, Laura Hartmann

  • 1Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.

The Journal of Organic Chemistry
|April 11, 2012
PubMed
Summary

Researchers developed a new solid-phase synthesis for creating sequence-defined, asymmetrically branched poly/oligo(amidoamines) (PAAs). This method allows for diverse side chain introduction, enhancing potential for gene delivery applications.

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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
13:42

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

Published on: November 2, 2011

Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Biomaterials

Background:

  • Sequence-defined polymers offer precise control over structure and function.
  • Poly/oligo(amidoamines) (PAAs) are versatile macromolecules with potential in biomedical applications.
  • Current synthesis methods for branched PAAs are limited in achieving asymmetry and side-chain diversity.

Purpose of the Study:

  • To develop a novel solid-phase synthesis for asymmetrically branched, sequence-defined PAAs.
  • To introduce new building blocks and protecting group strategies for enhanced synthetic control.
  • To explore the potential of these PAAs as nonviral vectors for gene delivery.

Main Methods:

  • Utilized solid-phase synthesis with Fmoc/Alloc/Boc protecting group strategy.
  • Introduced two new diethylenetriamine building blocks for orthogonal on-resin cleavage.
  • Demonstrated automated multiple on-resin cleavage of Alloc groups for asymmetrical branching.
  • Incorporated side chains of varying length and number.

Main Results:

  • Successfully synthesized asymmetrically branched, sequence-defined PAAs for the first time.
  • Established an Fmoc/Alloc/Boc strategy enabling orthogonal protection and cleavage.
  • Showcased the ability to introduce diverse side chains and control branching patterns.
  • Generated PAAs with tunable backbone lengths and sequences.

Conclusions:

  • The developed solid-phase synthesis provides unprecedented control over PAA architecture.
  • These asymmetrically branched PAAs are promising candidates for nonviral gene delivery vectors.
  • Further studies can correlate PAA branching with biological properties for optimized gene therapy applications.