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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

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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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Protein Folding01:25

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Proteins are chains of amino acids linked together by peptide bonds. Upon synthesis, a protein folds into a three-dimensional conformation, critical to its biological function. Interactions between its constituent amino acids guide protein folding, and hence the protein structure is primarily dependent on its amino acid sequence.
Protein Structure Is Critical to Its Biological Function
Proteins perform a wide range of biological functions such as catalyzing chemical reactions, providing...
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Preparation of Amides01:29

Preparation of Amides

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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...
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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.
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ATP and Macromolecule Synthesis01:28

ATP and Macromolecule Synthesis

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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...
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Protein Organization01:24

Protein Organization

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Proteins are polymers of amino acid residues. They are versatile and responsible for different cellular functions, including DNA replication, molecular transport, catalysis, and structural support. Proteins have a hierarchical structure comprising at least three levels of organization: primary, secondary, and tertiary structure. Some large proteins have a quaternary structure where individual protein subunits are linked together.
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Approaches for peptide and protein cyclisation.

Heather C Hayes1, Louis Y P Luk2, Yu-Hsuan Tsai3

  • 1School of Chemistry, Cardiff University, Cardiff, CF10 3AT, UK.

Organic & Biomolecular Chemistry
|May 12, 2021
PubMed
Summary

Polypeptide cyclisation enhances biological function, stability, and resistance to degradation. This review categorizes chemical, enzymatic, and protein tag methods for creating cyclic peptides.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Synthetic Chemistry

Background:

  • Polypeptide cyclisation is vital for biological functions, stability, and proteolytic resistance.
  • Diverse cyclisation strategies exist, applicable in vitro and in vivo.
  • Understanding these methods is key for peptide engineering.

Purpose of the Study:

  • To review and categorize existing polypeptide cyclisation methods.
  • To discuss the features and selection criteria for different cyclisation approaches.
  • To provide a comprehensive resource for researchers in peptide chemistry.

Main Methods:

  • Categorization of cyclisation techniques into chemical, enzymatic, and protein tag strategies.
  • Detailed description of specific chemical methods: direct backbone cyclisation, native chemical ligation, aldehyde-based ligations, bioorthogonal reactions, and disulphide formation.
  • Overview of enzymatic methods: subtiligase variants, sortases, asparaginyl endopeptidases, transglutaminases, and non-ribosomal peptide synthetases.
  • Exploration of protein tag approaches: inteins and engineered protein domains for isopeptide bond formation.

Main Results:

  • A systematic classification of polypeptide cyclisation methods is presented.
  • Key features and advantages of each method are discussed.
  • Considerations for selecting the most appropriate cyclisation strategy are outlined.

Conclusions:

  • The review provides a comprehensive overview of current polypeptide cyclisation technologies.
  • Informed selection of cyclisation methods can be guided by the discussed features and criteria.
  • Advancements in polypeptide cyclisation will continue to impact peptide-based therapeutics and research.