Issue 10, 2023

Chirality: a key parameter in chemical probes

Abstract

Many small molecule bioactive and marketed drugs are chiral. They are often synthesised from commercially available chiral building blocks. However, chirality is sometimes incorrectly assigned by manufacturers with consequences for the end user ranging from: experimental irreproducibility, wasted time on synthesising the wrong product and reanalysis, to the added cost of purchasing the precursor and resynthesis of the correct stereoisomer. Further on, this could lead to loss of reputation, loss of funding, to safety and ethical concerns due to potential in vivo administration of the wrong form of a drug. It is our firm belief that more stringent control of chirality be provided by the supplier and, if needed, requested by the end user, to minimise the potential issues mentioned above. Certification of chirality would bring much needed confidence in chemical structure assignment and could be provided by a variety of techniques, from polarimetry, chiral HPLC, using known chiral standards, vibrational circular dichroism, and x-ray crystallography. A few case studies of our brushes with wrong chirality assignment are shown as well as some examples of what we believe to be good practice.

Graphical abstract: Chirality: a key parameter in chemical probes

Supplementary files

Article information

Article type
Opinion
Submitted
02 Jun 2023
Accepted
01 Aug 2023
First published
08 Aug 2023
This article is Open Access
Creative Commons BY license

RSC Chem. Biol., 2023,4, 716-721

Chirality: a key parameter in chemical probes

A. McGown, J. Nafie, M. Otayfah, S. Hassell-Hart, G. J. Tizzard, S. J. Coles, R. Banks, G. P. Marsh, H. J. Maple, G. E. Kostakis, I. Proietti Silvestri, P. Colbon and J. Spencer, RSC Chem. Biol., 2023, 4, 716 DOI: 10.1039/D3CB00082F

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