RDChiral: An RDKit Wrapper for Handling Stereochemistry in Retrosynthetic Template Extraction and Application
Name
RDChiral__An_RDKit_Wrapper_for_Handling_Stereochemistry_in_Retrosynthetic_Template_Extraction_and_Application_v1.pdf
Description
Accepted version
Size
473.41 KB
Format
Adobe PDF
Checksum (MD5)
04b4cead2262a2efb38ee904f09b5585
Author(s)
Coley, Connor W
Green, William H
Jensen, Klavs F
Date Issued
2019
Journal
Journal of Chemical Information and Modeling
Publisher
American Chemical Society (ACS)
Version
Author's final manuscript
Abstract
© 2019 American Chemical Society. There is a renewed interest in computer-aided synthesis planning, where the vast majority of approaches require the application of retrosynthetic reaction templates. Here we introduce RDChiral, an open-source Python wrapper for RDKit designed to provide consistent handling of stereochemical information in applying retrosynthetic transformations encoded as SMARTS strings. RDChiral is designed to enforce the introduction, destruction, retention, and inversion of chiral tetrahedral centers as well as the cis/trans configuration of double bonds. We also introduce an open-source implementation of a retrosynthetic template extraction algorithm to generate SMARTS patterns from atom-mapped reaction SMILES strings. In this application note, we describe the implementation of these two pieces of code and illustrate their use through many examples.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/acs.jcim.9b00286
