SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction
Abstract
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.
Citation
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
Publication
ChemBioChem
Status
Peer reviewed
ISSN
1439-4227Type
Journal article
Description
This 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.Collections
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