Related Experiment Video
Updated: Jun 8, 2025

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Significant Chiral Asymmetry Observed in Neutral Amino Acid Ultraviolet Photolysis
Brendan Moore1, Linshan Zeng1, Pavle Djuricanin1
1Department of Chemistry, The University of British Columbia, Vancouver, BC V6T 1Z1, Canada.
Abstract:
The origin of homochirality in biological organisms remains an open question. Some suggest that its origin might be extraterrestrial, specifically due to the exposure of chiral molecules to circularly polarized photons in interstellar space, which could cause an initial population imbalance leading to the homochirality observed today. However, this extraterrestrial hypothesis has not been widely accepted, largely due to the belief that molecular optical rotatory dispersion is too insignificant to create the substantial imbalance required for homochirality. Here we report experimental evidence that specific conformers of neutral amino acids exhibit significant asymmetry in the chiral destroying dissociation rate induced by circularly polarized photons. The observed anisotropy factor for the lowest energy conformer of leucine was remarkably large, reaching 0.1─a factor of 13 times larger than observed for zwitterionic leucine in solid films, and nearly 40 times greater than the anisotropy reported in the electronic absorption spectrum of gas-phase leucine ensembles at room temperature. This significant finding indicates that even if reported anisotropy values in the electronic absorption spectrum are low, the dissociation asymmetry of certain conformers can still be substantial. An anisotropy factor of 0.1 could result in an initial enantiomeric excess exceeding 10%, even with a 90% extent of reaction. This discovery suggests that asymmetric photodissociation of amino acids may have been a crucial factor in the emergence of biological homochirality.
Related Concept Videos
Chirality in Nature
Chirality
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...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Prochirality
Properties of Enantiomers and Optical Activity

