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

Alina Tirla | Zendy; Kevin M. Wernke | Zendy; Seth B. Herzon | Zendy

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

Author(s) -

Alina Tirla,

Kevin M. Wernke,

Seth B. Herzon

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01796

Subject(s) - chemistry , decarboxylation , oxazole , carboxylic acid , ring (chemistry) , hydrolysis , chemical shift , stereochemistry , organic chemistry , medicinal chemistry , catalysis

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.

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