Reaction profiles for quantum chemistry-computed [3 + 2] cycloaddition reactions
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s41597-023-01977-8.pdf
Description
Published version
Size
3.2 MB
Format
Adobe PDF
Checksum (MD5)
0db8449ccbb608d7ea518d014556b086
Author(s)
Stuyver, Thijs
Jorner, Kjell
Coley, Connor W
Date Issued
2023
Journal
Scientific Data
Publisher
Springer Science and Business Media LLC
Citation
Stuyver, T., Jorner, K. & Coley, C.W. Reaction profiles for quantum chemistry-computed [3 + 2] cycloaddition reactions. Sci Data 10, 66 (2023).
Version
Final published version
Abstract
Bio-orthogonal click chemistry based on [3 + 2] dipolar cycloadditions has had a profound impact on the field of biochemistry and significant effort has been devoted to identify promising new candidate reactions for this purpose. To gauge whether a prospective reaction could be a suitable bio-orthogonal click reaction, information about both on- and off-target activation and reaction energies is highly valuable. Here, we use an automated workflow, based on the autodE program, to compute over 5000 reaction profiles for [3 + 2] cycloadditions involving both synthetic dipolarophiles and a set of biologically-inspired structural motifs. Based on a succinct benchmarking study, the B3LYP-D3(BJ)/def2-TZVP//B3LYP-D3(BJ)/def2-SVP level of theory was selected for the DFT calculations, and standard conditions and an (aqueous) SMD model were imposed to mimic physiological conditions. We believe that this data, as well as the presented workflow for high-throughput reaction profile computation, will be useful to screen for new bio-orthogonal reactions, as well as for the development of novel machine learning models for the prediction of chemical reactivity more broadly.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Electrical Engineering and Computer Science
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Creative Commons Attribution
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DOI of Published Version
https://doi.org/10.1038/s41597-023-01977-8
