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Related Concept Videos

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...
Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...
Ion-Exchange Chromatography01:09

Ion-Exchange Chromatography

Ion-exchange chromatography, or IEC, is a technique for separating ions based on their affinity for the stationary phase. The stationary phase is a cross-linked polymer resin with covalently attached ionic functional groups. The functional groups can be either positively charged (cation exchangers) or negatively charged (anion exchangers). A cation exchanger consists of a polymeric anion and active cations, while an anion exchanger is a polymeric cation with active anions. The choice of...
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,...
Peptide Identification Using Tandem Mass Spectrometry01:33

Peptide Identification Using Tandem Mass Spectrometry

Tandem mass spectrometry, also known as MS/MS or MS2, is an analytical technique that employs two mass analyzers. Essentially it is a series of mass spectrometers that helps isolate a particular biomolecule and then helps study its chemical properties.
This technique helps gather information regarding the protein from which the peptide was obtained and to study the peptides’ amino acid sequence. Identifying peptides from a complex mixture is an important component of the growing field of...

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Related Experiment Video

Updated: May 18, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Controllable core-shell-type resin for solid-phase peptide synthesis.

Hong-Jun Cho1, Tae-Kyung Lee, Jung Won Kim

  • 1School of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea.

The Journal of Organic Chemistry
|September 27, 2012
PubMed
Summary

A novel core-shell resin was developed for efficient solid-phase peptide synthesis (SPPS). This resin excels in synthesizing challenging peptide sequences, including hydrophobic and aggregative ones, outperforming standard resins.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Solid-phase peptide synthesis (SPPS) relies on functionalized resins for efficient peptide chain elongation.
  • Conventional resins like aminomethyl polystyrene (AM PS) can present challenges with hydrophobic or complex peptide sequences.
  • Developing advanced resin architectures is crucial for improving SPPS efficiency and scope.

Purpose of the Study:

  • To develop a simple, mild, and cost-effective biphasic functionalization method for creating core-shell resins.
  • To investigate the controlled synthesis and characterization of core-shell resin architecture.
  • To evaluate the performance of the novel core-shell resin in solid-phase peptide synthesis (SPPS) compared to existing resins.

Main Methods:

  • Biphasic functionalization of aminomethyl polystyrene (AM PS) resin with Fmoc-OSu to create a core-shell structure.
  • Characterization of shell layer thickness using confocal laser scanning microscopy (CLSM).
  • Demonstration of efficiency through the synthesis of various peptides, including hydrophobic sequences, a disulfide-bridged cyclic peptide, and a PNA sequence, with comparisons to AM PS and PEG-based resins.

Main Results:

  • A core-shell-type resin was successfully prepared using a mild and inexpensive biphasic functionalization approach.
  • The shell layer thickness of the core-shell resin was controllable and characterized by CLSM.
  • The core-shell resin demonstrated superior performance in synthesizing hydrophobic peptides, a cyclic peptide, and a difficult PNA sequence.
  • Efficient synthesis of the highly aggregative peptide fragment MoPrP 105-125 was achieved on the core-shell resin under microwave conditions, outperforming AM PS and ChemMatrix resins.

Conclusions:

  • The developed core-shell resin offers an ideal architecture for advanced solid-phase peptide synthesis.
  • This novel resin facilitates the efficient synthesis of challenging peptide sequences, including highly aggregative ones.
  • The biphasic functionalization method provides a versatile and effective strategy for resin modification in peptide chemistry.