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Related Concept Videos

Histone Modification02:32

Histone Modification

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The histone proteins have a flexible N-terminal tail extending out from the nucleosome. These histone tails are often subjected to post-translational modifications such as acetylation, methylation, phosphorylation, and ubiquitination. Particular combinations of these modifications form “histone codes” that influence the chromatin folding and tissue-specific gene expression.
Acetylation
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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...
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Cytoskeletal Linker Proteins - Plakins01:09

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Plakins are large proteins with binding domains for microtubules, microfilaments, intermediate filaments, and membrane-associated protein complexes at cell junctions. Plakin functions are evolutionarily conserved and are primarily involved in organizing the different components of the cytoskeleton by crosslinking them to each other and connecting them to the cell-matrix and cell adhesion complexes. They are also known to interact with signal transducers, serve as scaffolds for signaling...
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The histone proteins in the nucleosomes are post-translationally modified (PTM) to increase or decrease access to DNA. The commonly observed PTMs are methylation, acetylation, phosphorylation, and ubiquitination of lysine amino acids in the histone H3 tail region. These histone modifications have specific meaning for the cell. Hence, they are called "histone code". The protein complex involved in histone modification is termed as "reader-writer" complex.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Direct Peptide Cyclization and One-Pot Modification Using the MeDbz Linker.

Bengt H Gless1, Christian A Olsen1

  • 1Center for Biopharmaceuticals and Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences , University of Copenhagen , Universitetsparken 2 , DK-2100 Copenhagen , Denmark.

The Journal of Organic Chemistry
|August 7, 2018
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Summary

This study introduces a novel one-pot method for synthesizing and modifying cyclic peptides using a self-cleaving resin protocol. This efficient approach enables direct cyclization and subsequent modifications like fluorophore conjugation for diverse peptide applications.

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Area of Science:

  • Organic Chemistry
  • Peptide Chemistry
  • Synthetic Biology

Background:

  • Cyclic peptides are crucial in drug discovery and biological research.
  • Efficient synthesis and modification of cyclic peptides remain challenging.
  • Existing methods often require multiple steps and harsh conditions.

Purpose of the Study:

  • To develop a streamlined one-pot protocol for cyclic peptide synthesis and modification.
  • To demonstrate the versatility of the method for natural product synthesis.
  • To enable direct post-synthesis modifications of cyclic peptides.

Main Methods:

  • Utilized a self-cleaving on-resin protocol with Dawson's MeDbz linker.
  • Employed thioesterification followed by S → N acyl shift for intramolecular cyclization.
  • Applied native chemical ligation without activating additives.

Main Results:

  • Successfully synthesized 5 cyclic peptide natural products of varying ring sizes.
  • Achieved direct intramolecular peptide cyclization.
  • Demonstrated one-pot modifications including desulfurization, fluorophore conjugation, and disulfide bond formation.

Conclusions:

  • The developed one-pot strategy offers an efficient and versatile approach to cyclic peptide synthesis and modification.
  • This method simplifies the preparation of complex cyclic peptides and their derivatives.
  • The protocol facilitates direct functionalization for diverse applications, including bioconjugation and drug development.