Precursor-directed biosynthesis of catechol compounds in Acinetobacter bouvetii DSM 14964. Issue 81 (14th September 2020)

• Record Type: Journal Article
• Authors: Reitz, Zachary L.; Butler, Alison
• Is Part Of: Chemical communications. Volume 56:Issue 81(2020)
• Page Start: 12222
• Page End: 12225
• Publication Date: 2020-09-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc04171h
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Genome mining for VibH homologs reveals several Acinetobacter species with a gene cluster putatively encoding biosynthesis of catechol siderophores with an amine core. Enzyme flexibility allows for in vivo synthesis of non-native catechol compounds. Abstract : Genome mining for VibH homologs reveals several species of Acinetobacter with a gene cluster that putatively encodes the biosynthesis of catechol siderophores with an amine core. A. bouvetii DSM 14964 produces three novel biscatechol siderophores: propanochelin (1 ), butanochelin (2 ), and pentanochelin (3 ). This strain has a relaxed specificity for the amine substrate, allowing for the biosynthesis of a variety of non-natural siderophore analogs by precursor directed biosynthesis. Of potential synthetic utility, A. bouvetii DSM 14964 condenses 2, 3-dihydroxybenzoic acid (2, 3-DHB) to allylamine and propargylamine, producing catecholic compounds which bind iron(iii ) and may be further modified via thiol–ene or azide–alkyne click chemistry.