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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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Formal Charges02:42

Formal Charges

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In some cases, there are seemingly more than one valid Lewis structures for molecules and polyatomic ions. The concept of formal charges can be used to help predict the most appropriate Lewis structure when more than one reasonable structure exists.
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Bonding in Metals02:32

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Metallic bonds are formed between two metal atoms. A simplified model to describe metallic bonding has been developed by Paul Drüde called the “Electron Sea Model”. 
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Ionic Bonds00:42

Ionic Bonds

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Overview
When atoms gain or lose electrons to achieve a more stable electron configuration they form ions. Ionic bonds are electrostatic attractions between ions with opposite charges. Ionic compounds are rigid and brittle when solid and may dissociate into their constituent ions in water. Covalent compounds, by contrast, remain intact unless a chemical reaction breaks them.
Opposing Charges Hold Ions Together in Ionic Compounds
Ionic bonds are reversible electrostatic interactions between ions...
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Covalent Bonds01:29

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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
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Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Characterization of Intra-Cartilage Transport Properties of Cationic Peptide Carriers
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Probing Charge Transport through Peptide Bonds.

Joseph M Brisendine1, Sivan Refaely-Abramson2,3, Zhen-Fei Liu2,3

  • 1Graduate Programs of Physics, Biology, Chemistry and Biochemistry, The Graduate Center of CUNY, New York, and Department of Biochemistry, City College of New York , New York, New York 10031, United States.

The Journal of Physical Chemistry Letters
|January 30, 2018
PubMed
Summary
This summary is machine-generated.

Single-molecule conductance measurements reveal that peptide bonds significantly reduce electrical conductivity compared to alkanes. This finding, attributed to charge localization, impacts the conductance decay of peptide chains.

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Area of Science:

  • Molecular Electronics
  • Supramolecular Chemistry
  • Surface Science

Background:

  • Understanding charge transport in organic molecules is crucial for molecular electronics.
  • Peptides, as fundamental biomolecular building blocks, offer unique structural and electronic properties.
  • Previous studies have explored conductance of molecules, but direct comparison with peptide bonds is limited.

Purpose of the Study:

  • To measure and analyze the single-molecule electrical conductance of unmodified peptides.
  • To elucidate the impact of peptide bonds on charge transport compared to saturated hydrocarbon chains.
  • To investigate the underlying electronic mechanisms responsible for observed conductance differences.

Main Methods:

  • Utilized scanning tunneling microscope-break junction (STM-BJ) technique for single-molecule conductance measurements.
  • Employed N-terminal amine and C-terminal carboxyl groups as anchoring points to gold electrodes.
  • Performed first-principles calculations to model electronic structure and charge transport properties.

Main Results:

  • Peptide bonds in oligoglycine and oligoalanine were found to decrease conductance compared to analogous alkanes.
  • Conductance decay with increasing molecular length was more pronounced in peptides than in alkanes.
  • Theoretical calculations attributed conductance reduction to charge localization at peptide bonds, affecting orbital energies and coupling.

Conclusions:

  • Peptide bonds act as intrinsic barriers to charge transport at the single-molecule level.
  • The electronic structure of the peptide backbone significantly influences molecular conductance.
  • Findings provide fundamental insights into the electrical properties of peptides for molecular electronic applications.