Issue 41, 2022

Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

Abstract

The molecular origins of homochirality on Earth is not understood well, particularly how enantiomerically enriched molecules of astrobiological significance like sugars and amino acids might have been synthesized on icy grains in space preceding their delivery to Earth. Polycyclic aromatic hydrocarbons (PAHs) identified in carbonaceous chondrites could have been processed in molecular clouds by circularly polarized light prior to the depletion of enantiomerically enriched helicenes onto carbonaceous grains resulting in chiral islands. However, the fundamental low temperature reaction mechanisms leading to racemic helicenes are still unknown. Here, by exploiting synchrotron based molecular beam photoionization mass spectrometry combined with electronic structure calculations, we provide compelling testimony on barrierless, low temperature pathways leading to racemates of [5] and [6]helicene. Astrochemical modeling advocates that gas-phase reactions in molecular clouds lead to racemates of helicenes suggesting a pathway for future astronomical observation and providing a fundamental understanding for the origin of homochirality on early Earth.

Graphical abstract: Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

Supplementary files

Article information

Article type
Paper
Submitted
07 Jul 2022
Accepted
21 Aug 2022
First published
03 Sep 2022

Phys. Chem. Chem. Phys., 2022,24, 25077-25087

Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

R. I. Kaiser, L. Zhao, W. Lu, M. Ahmed, M. M. Evseev, V. N. Azyazov, A. M. Mebel, R. K. Mohamed, F. R. Fischer and X. Li, Phys. Chem. Chem. Phys., 2022, 24, 25077 DOI: 10.1039/D2CP03084E

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