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. 2022 Aug 30;12:14737. doi: 10.1038/s41598-022-19040-8

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© The Author(s) 2022

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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The Dep pathway. The C3 OH group of DON (shown in red) is stereochemically inverted to produce the diastereomer, 3-epi-DON. In the expanded image of this stereogenic center, R₁ and R₂ represent the priority groups attached to the sp² hybridized C3. Hydride attack on the re-face at the prochiral C3 center generates 3-epi-DON.