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Chirality in Nature

Chirality in Nature

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.

Prochirality

Prochirality

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...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

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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Assembly of Gold Nanorods into Chiral Plasmonic Metamolecules Using DNA Origami Templates

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Reversible chirality control in peptide-functionalized gold nanoparticles.

Edoardo Longo¹, Andrea Orlandin, Fabrizio Mancin

¹Department of Chemical Sciences, University of Padova , Via Marzolo 1, 35131 Padova, Italy.

|October 17, 2013

Summary

Chiral gold nanoparticles exhibit tunable chiroptical properties influenced by peptide structure. Chirality can be reversibly controlled by temperature, offering new possibilities for nanomaterial applications.

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Area of Science:

Nanotechnology
Supramolecular Chemistry
Biophysics

Background:

Gold nanoparticles (AuNPs) are widely studied for their unique optical properties.
Peptide passivation of nanoparticles is crucial for stability and functionality.
Inducing chirality in achiral nanomaterials is a significant challenge.

Purpose of the Study:

To investigate the induction of chiroptical properties in gold nanoparticles using peptide passivation.
To explore the relationship between peptide sequence, secondary structure, and nanoparticle chirality.
To determine the influence of temperature on the chiroptical response of these systems.

Main Methods:

Synthesis of 2 nm gold nanoparticles.
Passivation with short peptides containing Aib-l-Ala repeats.
Characterization of chiroptical properties using electronic circular dichroism (ECD) spectroscopy.
Temperature-dependent measurements to assess chirality reversibility.

Main Results:

AuNPs functionalized with short peptides exhibited significant ECD signals in the 300-650 nm range.
Chiroptical response depended on the number of amino acids (odd/even) in the peptide chain, mimicking enantiomers.
Chirality was linked to peptide secondary structure and diminished with longer sequences adopting a 310-helix.
Chirality was reversibly controlled by temperature variations.

Conclusions:

Peptide secondary structure on nanoparticle surfaces dictates induced chiroptical properties.
The number of amino acids in the peptide chain is critical for observing mirror-image ECD spectra.
Temperature provides a reversible switch for controlling nanoparticle chirality, opening avenues for dynamic nanomaterials.