A Novel Microbial Biotransformation Method has been Developed to resolve 4-oxo-4,5,6,7-tetrahydrobenzofuran Derivatives

Year 2025, Volume: 12 Issue: 3, 189 - 196, 14.09.2025

Zerrin Zerenler Çalışkan , Leyla Yılmaz Kara

https://doi.org/10.18596/jotcsa.1712808

Abstract

There is a recognized need for new and improved methods for constructing pharmacologically important heterocyclic systems. In this context, enhancing methods for preparing chiral benzofuranone derivatives has become significantly important. Aspergillus species are versatile fungi that play a crucial role in the asymmetric synthesis of chiral building blocks and are involved in various biological processes. In this study, the microbial biotransformation of 4-oxo-tetrahydrobenzofuran derivatives was investigated for the first time in the literature through catalysis by Aspergillus species. This process was mediated by the fungi A. niger ATCC 6275 and A. oryzae RIB40. Acetoxy (3) and hydroxy (4) benzofuranone derivatives formed as a result of the biotransformation reaction have been obtained with high enantiomeric purity. The results obtained from this study were compared to those from our previous research using lipase enzymes. This study shows that the microbial biotransformation of 4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran derivatives is more effective than enzymatic biotransformation. Based on the findings of this study, a comprehensive review of the stereoselective biotransformation reactions of 4-oxo-tetrahydrobenzofuran derivatives is presented.

Keywords

microbial biotransformation , Aspergillus species , benzofuranone

Ethical Statement

The authors affirm that they do not have any competing interests. It does not require ethics approval.

Supporting Institution

Yildiz Technical University

Project Number

BAP(FBA-2023-4736-GAP)

Thanks

Financial support from the Yildiz Technical University (FBA-2023-4736-GAP) is greatly appreciated.

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