Work

On the Stability and Spectroscopic Properties of 5-Hydroxyoxazole-4-carboxylic Acid Derivatives

Year: 2021

Type: article

Abstract: 5-Hydroxyoxazole-4-carboxylic acid residues were advanced as substructures within the secondary bacterial metabolites precolibactins 969 and 795a. However, oxazoles containing both 5-hydroxy and 4-carboxy substituents are unprecedented. We have found these oxazoles are unstable with respect to hydrolytic ring opening and decarboxylation. Comparison of reported and theoretical 13 C NMR chemical shifts between synthetic intermediates and the isolates revealed discrepancies in the oxazole region. These results suggest that precolibactins 969 and 795a may not contain 5-hydroxyoxazole-4-carboxylic acid residues.

Source: Organic Letters

DOI: 10.1021/acs.orglett.1c01796

Authors: Alina Tirla, Kevin M. Wernke, Seth B. Herzon

Institution: Yale University

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology (medical)

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funders: Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, National Institutes of Health, National Cancer Institute, National Institute of General Medical Sciences

Awards: Synthesis of precolibactin-969 and related metabolites. Characterization of their DNA-damaging activities., Predoctoral Training at the Interface Chemistry and Biology, Structural and functional studies of colibactin