SynBio-SynChem Approaches to Diversifying the Pacidamycins through the Exploitation of an Observed Pictet-Spengler Reaction

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dc.contributor.authorCartmell, Christopher
dc.contributor.authorAbou Fayad, Antoine G.
dc.contributor.authorLynch, Rosemary
dc.contributor.authorSharma, Sunil Vishnuprasadji
dc.contributor.authorHauck, Nils
dc.contributor.authorGust, Bertolt
dc.contributor.authorGoss, Rebecca J.M.
dc.contributor.departmentExperimental Pathology, Microbiology, and Immunology
dc.contributor.facultyFaculty of Medicine (FM)
dc.contributor.institutionAmerican University of Beirut
dc.date.accessioned2025-01-24T11:39:06Z
dc.date.available2025-01-24T11:39:06Z
dc.date.issued2021
dc.description.abstractA 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. © 2020 The Authors. ChemBioChem published by Wiley-VCH GmbH
dc.identifier.doihttps://doi.org/10.1002/cbic.202000594
dc.identifier.eid2-s2.0-85099446862
dc.identifier.pmid33058439
dc.identifier.urihttp://hdl.handle.net/10938/29176
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.relation.ispartofChemBioChem
dc.sourceScopus
dc.subjectCompound diversification
dc.subjectNatural products
dc.subjectPacidamycin
dc.subjectPictet-spengler
dc.subjectSemisynthesis
dc.subjectUridyl peptide antibiotic
dc.subjectAnti-bacterial agents
dc.subjectOligopeptides
dc.subjectPeptides
dc.subjectStreptomyces
dc.subjectUridine
dc.subjectPacidamycin 4
dc.subjectPolypeptide antibiotic agent
dc.subjectTetrahydroisoquinoline
dc.subjectUnclassified drug
dc.subjectAntiinfective agent
dc.subjectOligopeptide
dc.subjectPeptide
dc.subjectAmino terminal sequence
dc.subjectArticle
dc.subjectBacterial strain
dc.subjectBacterium culture
dc.subjectDiastereoisomer
dc.subjectDiastereoselectivity
dc.subjectDrug synthesis
dc.subjectFermentation
dc.subjectGene
dc.subjectGene cluster
dc.subjectGene control
dc.subjectHorizontal gene transfer
dc.subjectIon exchange
dc.subjectLiquid chromatography-mass spectrometry
dc.subjectMic90
dc.subjectNonhuman
dc.subjectNpsm gene
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectPictet spengler reaction
dc.subjectPlasmid
dc.subjectPriority journal
dc.subjectProton nuclear magnetic resonance
dc.subjectPseudomonas aeruginosa
dc.subjectReversed phase liquid chromatography
dc.subjectStreptomyces coeruleorubidus
dc.subjectMetabolism
dc.subjectSynthesis
dc.titleSynBio-SynChem Approaches to Diversifying the Pacidamycins through the Exploitation of an Observed Pictet-Spengler Reaction
dc.typeArticle

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