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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

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Properties of Enantiomers and Optical Activity

Properties of Enantiomers and Optical Activity

It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...

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A Micropatterning Assay for Measuring Cell Chirality

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Published on: March 11, 2022

Orientational Chirality, Its Asymmetric Control, and Computational Study.

Shengzhou Jin¹, Yu Wang¹, Yao Tang²

¹School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

Research (Washington, D.C.)

|September 18, 2024

Summary

A new model for orientational chirality was discovered, featuring a C(sp)-C(sp³) axis and remote blocking groups. This model differs from traditional ones and enables stereoselective synthesis of chiral molecules.

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Published on: February 15, 2016

Area of Science:

Stereochemistry
Organic Chemistry
Computational Chemistry

Background:

Traditional models like Felkin-Ahn and Cram involve adjacent chiral centers and blocking groups.
Rotation around adjacent C(sp²)-C(sp³) axes in traditional models presents six energy barriers.
A new understanding of chirality is needed to explain observed stereochemical outcomes.

Purpose of the Study:

To discover and characterize a new type of chirality: orientational chirality.
To propose a novel model system for orientational chirality distinct from existing models.
To demonstrate the utility of this new model in asymmetric synthesis and stereochemical control.

Main Methods:

X-ray structural analysis to confirm orientatiomer stabilization by through-space functional groups.
Development of a new model focusing on the steric interaction between a chiral C(sp)-C(sp³) center and a remote blocker.
Utilizing chiral amide auxiliaries for stereoselective control of orientatiomer rotations.
Employing Suzuki-Miyaura and Sonogashira cross-coupling reactions for asymmetric synthesis.
Density functional theory (DFT) calculations to determine optimized conformers and relative energies.

Main Results:

Discovery of orientational chirality, characterized by a C(sp)-C(sp³) axis and a remote blocker.
The new model involves only three energy barriers for rotation around the chiral C(sp)-C(sp³) stereogenic unit.
Complete stereoselectivity was achieved using chiral amide auxiliaries.
Successful asymmetric synthesis of individual orientatiomers was accomplished.
DFT studies provided optimized structures and energy profiles for the orientational isomers.

Conclusions:

Orientational chirality offers a new paradigm in stereochemistry, fundamentally different from traditional models.
The proposed model provides a more accurate representation of steric interactions in certain chiral systems.
This discovery has potential applications in chemical, biomedical, and material sciences, opening new avenues for stereoselective synthesis.