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software_failure_32_ChemRxiv.pdf (1.38 MB)
Recent Advances in Stereochemistry Reveal Classification Shortcomings
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 16.06.2020 and posted on 18.06.2020by 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.