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Related Concept Videos

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.
Hydrogen Bonds Control the World!
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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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Aldehydes and Ketones with Water: Hydrate Formation01:20

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An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
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Radical Formation: Homolysis00:54

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications
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Histidine-based hydrogels via singlet-oxygen photooxidation.

Michelle S Liberato1, Nayara G S Cavalcante1, P Abinaya Sindu1

  • 1Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, 05508-000, São Paulo, Brazil. catalani@usp.br.

Soft Matter
|November 23, 2021
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Summary

Histidine-derived polymers form novel hydrogels via photosensitized oxidation and crosslinking. This method utilizes singlet oxygen to create covalent bonds, showing potential for new biomaterial development.

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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Biochemistry

Background:

  • Hydrogels are crucial in biomedical applications.
  • Developing novel crosslinking methods is essential for advanced hydrogel properties.
  • Histidine offers unique photo-oxidizable properties.

Purpose of the Study:

  • To demonstrate hydrogel formation from histidine-derived polymers using photosensitized oxidation.
  • To investigate the crosslinking mechanism involving histidine and singlet oxygen.
  • To evaluate the properties of newly formed histidine-based hydrogels.

Main Methods:

  • Photosensitized oxidation of pendant histidine residues using singlet oxygen.
  • Covalent crosslinking via histidine dimerization.
  • Functionalization of chondroitin sulfate (CS) and elastin-like peptides (ELPs) with histidine.
  • Irradiation at 425 nm in the presence of Zn-porphyrin derivatives.
  • Computer simulations to study ELP-His structure-property relationships.

Main Results:

  • Successful formation of histidine-based hydrogels from both CS-His and ELP-His.
  • Demonstrated crosslinking mechanism through photooxidation and dimerization of histidine.
  • ELP-His and other ELPs with photo-oxidizable amino acids were studied in silico.
  • A correlation between protein conformation and elastic properties was observed.
  • CS-His hydrogels exhibited higher storage moduli compared to ELPs with other amino acids.

Conclusions:

  • Photooxidation is a viable method for creating novel histidine-based hydrogels.
  • Histidine-derived polymers show promise for developing advanced hydrogel materials.
  • The study highlights the potential of controlled photo-crosslinking for biomaterial design.