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SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction
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dc.contributor.author | Cartmell, Christopher | |
dc.contributor.author | Abou Fayad, Antoine | |
dc.contributor.author | Lynch, Rosemary | |
dc.contributor.author | Sharma, Sunil | |
dc.contributor.author | Hauck, Nils | |
dc.contributor.author | Gust, Bertolt | |
dc.contributor.author | Goss, Rebecca Jane Miriam | |
dc.date.accessioned | 2021-01-15T15:30:02Z | |
dc.date.available | 2021-01-15T15:30:02Z | |
dc.date.issued | 2021-02-15 | |
dc.identifier | 270734391 | |
dc.identifier | 91de2602-de34-4c97-bbf4-68d0585e56c6 | |
dc.identifier | 85099446862 | |
dc.identifier | 000607641000001 | |
dc.identifier.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 | en |
dc.identifier.issn | 1439-4227 | |
dc.identifier.other | RIS: urn:62CD94343E4A95F94E2C7A50E3DEAA16 | |
dc.identifier.other | ORCID: /0000-0002-9726-0196/work/146014269 | |
dc.identifier.uri | https://hdl.handle.net/10023/21275 | |
dc.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. | en |
dc.description.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. | |
dc.format.extent | 6 | |
dc.format.extent | 849679 | |
dc.language.iso | eng | |
dc.relation.ispartof | ChemBioChem | en |
dc.subject | Pictet-Spengler | en |
dc.subject | Natural products | en |
dc.subject | Semi-synthesis | en |
dc.subject | Compound diversification | en |
dc.subject | Uridyl peptide antibiotics (UPAs) | en |
dc.subject | QD Chemistry | en |
dc.subject | QH301 Biology | en |
dc.subject | RM Therapeutics. Pharmacology | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.subject.lcc | QH301 | en |
dc.subject.lcc | RM | en |
dc.title | SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | European Research Council | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/cbic.202000594 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | WLR/R1/170069 | en |
dc.identifier.grantnumber | GCGXC | en |
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