Structure Revision of N-Mercapto-4-formylcarbostyril Produced by Pseudomonas fluorescens G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]

Karel Guillemyn, Steven Ballet, Lumeng Ye, Pierre Cornelis, Ole Hammerich, Carsten Christophersen

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    An antibiotic substance isolated from Pseudomonas fluorescens strain G308 was earlier assigned the structure of N-mercapto-4-formylcarbostyril, but computational predictions of the H-1 and C-13 NMR magnetic shielding tensors show this structure to be incompatible with the published spectroscopic data. The same is true for six quinoline derivatives related to N-mercapto-4-formylcarbostyril by permutation of the O and S atoms. In contrast, 2-(2-hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde], isolated from Pseudomonas protegens Pf-5, together with the reduced derivative aeruginol, displays spectroscopic data identical with those of the alleged carbostyril derivative. In addition, the published H-1 and C-13 NMR data are in agreement with those calculated for aeruginaldehyde. We propose that aeruginaldehyde and aeruginol originate from the non-ribosomal peptide synthetase enzymes involved in the siderophores enantio-pyochelin (or pyochelin) biosynthetic pathways.
    Original languageEnglish
    JournalNatural Product Communications
    Volume9
    Issue number6
    Pages (from-to)789-794
    Number of pages6
    ISSN1934-578X
    Publication statusPublished - 2014

    Keywords

    • Computational Biology
    • Gene Expression Regulation, Bacterial
    • Gene Expression Regulation, Enzymologic
    • Molecular Structure
    • Phenols
    • Pseudomonas fluorescens
    • Quinolones
    • Sulfhydryl Compounds
    • Thiazoles
    • N-mercapto-4-formylcarbostyril
    • aeruginaldehyde
    • CHEMISTRY,
    • FOOD
    • NMR CHEMICAL-SHIFTS
    • BURKHOLDERIA-CEPACIA
    • CELL COMMUNICATION
    • NATURAL-PRODUCTS
    • PYOCHELIN
    • SIDEROPHORE
    • AERUGINOSA
    • ACID
    • ANTIFUNGAL
    • QUINOLOBACTIN
    • Pseudomonas protegens
    • N-Mercapto-4-formylcarbostyril
    • Aeruginaldehyde
    • IQS
    • (Enantio)pyochelin
    • Aeruginol

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