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software_failure_32_ChemRxiv.pdf (1.38 MB)

Recent Advances in Stereochemistry Reveal Classification Shortcomings

submitted on 16.06.2020, 07:26 and posted on 18.06.2020, 23:07 by Peter J. Canfield, Linda J. Govenlock, Jeffrey Reimers, Maxwell J. Crossley
We contend that the Polytope model utilized by IUPAC to specify stereoisomerism for species MLn with n > 3 should be universally applied. Such application recently led to the synthesis of isolable compounds displaying a new fundamental form of isomerism, akamptisomerism, pertinent to ML2 stereocenters. We review 443807 molecules that could be classified as akamptisomers. Some akamptisomers are described as being “wrong” by existing IUPAC rules, hindering molecular conception. For many classes of medicinal and technology-related molecules, software packages like ChemDraw mostly do not handle akamptisomers correctly, databases such as CAS provide 2D representations inconsistent with those presented in the original publications, and often the akamptisomeric identity of compounds remains unknown. These features hinder both human and machine-learning approaches to chemical design. Further, the existence of previously unrecognized isomeric forms has broad implications for patents and pharmaceutical-registration requirements. Hence, the immediate re-examination of stereochemistry is demanded.


National Natural Science Foundation of China Grant No. 11674212


Email Address of Submitting Author


Shanghai University, University of technology Sydney


China and Australia

ORCID For Submitting Author


Declaration of Conflict of Interest

no conflict of interest

Version Notes

This is version 1