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Related Concept Videos

Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Radical Halogenation: Stereochemistry01:33

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Halogenation of Alkenes02:46

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Chirality in Nature02:30

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly.

Slavko Kralj1,2, Ottavia Bellotto1, Evelina Parisi1

  • 1Chemical and Pharmaceutical Sciences Department, University of Trieste, Via Giorgieri 1, 34127 Trieste, Italy.

ACS Nano
|November 11, 2020
PubMed
Summary

This study introduces heterochiral diphenylalanine peptides that form homogeneous, transparent hydrogels. These biomaterials show excellent cell viability and overcome the cytotoxicity and uncontrolled assembly of traditional diphenylalanine materials.

Keywords:
chiralityd-amino acidshalogenationhydrogelspeptidesphenylalanineself-assembly

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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides

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Area of Science:

  • Supramolecular Chemistry
  • Biomaterials Science
  • Peptide Self-Assembly

Background:

  • Diphenylalanine (Phe-Phe) peptides are amyloidogenic building blocks for supramolecular materials.
  • Challenges with Phe-Phe include uncontrolled hierarchical assembly and cytotoxicity.
  • Heterochirality offers a potential strategy to address these limitations.

Purpose of the Study:

  • To investigate heterochirality as a method to control diphenylalanine self-assembly and material properties.
  • To develop a non-toxic, homogeneous diphenylalanine-based biomaterial for cell culture.
  • To explore the impact of halogenation on the self-organization and properties of heterochiral diphenylalanine.

Main Methods:

  • Synthesis of an unprotected heterochiral dipeptide (d-Phe-l-Phe).
  • Characterization of self-assembled structures using single-crystal X-ray diffraction (XRD).
  • Assessment of hydrogel properties, including transparency, thermoreversibility, and biocompatibility with fibroblast cells.
  • Exploration of fluorinated and iodinated d-Phe-l-Phe derivatives.

Main Results:

  • d-Phe-l-Phe self-organized into homogeneous nanofibrils forming a transparent, optically clear hydrogel.
  • The heterochiral dipeptide hydrogel supported excellent fibroblast cell proliferation and viability, outperforming tissue-culture plastic.
  • Halogenation modulated self-assembly: fluorination yielded nanotubes with intermediate bundling, while iodination disrupted nanotube formation, enhancing stability but reducing transparency and biocompatibility.

Conclusions:

  • Heterochirality effectively controls diphenylalanine self-assembly, yielding homogeneous, non-toxic supramolecular materials.
  • d-Phe-l-Phe hydrogels represent promising biocompatible substrates for cell culture applications.
  • Halogenation provides a route to fine-tune the properties of these peptide-based biomaterials.