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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...

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Targeted Antibody Blocking by a Dual-Functional Conjugate of Antigenic Peptide and Fc-III Mimetics (DCAF)
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Targeted Antibody Blocking by a Dual-Functional Conjugate of Antigenic Peptide and Fc-III Mimetics (DCAF)

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Bis(2-sulfanylethyl)amino native peptide ligation.

Nathalie Ollivier1, Julien Dheur, Reda Mhidia

  • 1CNRS UMR 8161, Univ Lille Nord de France, Institut Pasteur de Lille, IFR 142 Molecular and Cellular Medicine, 1 rue du Pr Calmette 59021 Lille Cedex, France.

Organic Letters
|October 23, 2010
PubMed
Summary

A new peptide ligation method, SEA ligation, creates native peptide bonds using a bis(2-sulfanylethyl)amino group. This technique, along with a novel solid support for fragment synthesis, expands peptide chemistry tools.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biochemistry

Background:

  • Peptide synthesis and modification are crucial in biochemistry and chemical biology.
  • Existing peptide ligation methods have limitations in scope or efficiency.
  • Native peptide bond formation is a key goal for creating complex peptides.

Purpose of the Study:

  • To introduce a novel chemoselective and regioselective peptide ligation method.
  • To develop a new solid support for synthesizing peptide fragments for ligation.
  • To expand the available tools for peptide chemists.

Main Methods:

  • Utilizing a bis(2-sulfanylethyl)amino (SEA) group on a C-terminal peptide.
  • Reacting the SEA-tagged peptide with a cysteinyl peptide in aqueous conditions (pH 7, 37 °C).
  • Developing and employing a novel solid support for Fmoc/tert-butyl solid phase peptide synthesis of SEA fragments.

Main Results:

  • Successful chemoselective and regioselective formation of a native peptide bond via SEA ligation.
  • Demonstration of SEA ligation in water under physiological conditions.
  • Straightforward synthesis of peptide SEA fragments using the new solid support and standard SPPS.

Conclusions:

  • SEA ligation is a valuable addition to the peptide chemist's toolkit for native peptide synthesis.
  • The developed solid support facilitates the preparation of SEA peptide fragments.
  • This method offers a new avenue for constructing peptides with native linkages.