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SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction

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Date
15/02/2021
Author
Cartmell, Christopher
Abou Fayad, Antoine
Lynch, Rosemary
Sharma, Sunil
Hauck, Nils
Gust, Bertolt
Goss, Rebecca Jane Miriam
Keywords
Pictet-Spengler
Natural products
Semi-synthesis
Compound diversification
Uridyl peptide antibiotics (UPAs)
QD Chemistry
QH301 Biology
RM Therapeutics. Pharmacology
DAS
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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
DOI
https://doi.org/10.1002/cbic.202000594
ISSN
1439-4227
Type
Journal article
Rights
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.
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.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/21275

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