SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction
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A nonenzymatic Pictet‐Spengler reaction has been postulated to give rise to a subset of naturally occurring uridyl peptide antibiotics (UPAs). Here, using a combination of strain engineering and synthetic chemistry, we demonstrate that Pictet‐Spengler chemistry may be employed to generate even greater diversity in the UPAs. We use an engineered strain to afford access to meta‐tyrosine containing pacidamycin 4. Pictet‐Spengler diversification of this compound using a small series of aryl‐aldehydes was achieved with some derivatives affording remarkable diastereomeric control.
Cartmell , C , Abou Fayad , A , Lynch , R , Sharma , S , Hauck , N , Gust , B & Goss , R J M 2021 , ' SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction ' , ChemBioChem , vol. 22 , no. 4 , pp. 712-716 . https://doi.org/10.1002/cbic.202000594
Copyright © 2020 The Authors. ChemBioChem published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
DescriptionThis work was supported by European Research Council under the European Union's Seventh Framework Programme (FP7-3013/ERC grant agreement no 614779 GenoChemetics) and Royal Society Wolfson SMART centre.
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