Work

Total Synthesis and Stereochemical Assignment of Alternapyrone

Year: 2025

Type: article

Abstract: Alternapyrone, a bioactive polyketide produced by the fungal host Aspergillus oryzae, is biosynthesized by a polyketide synthase encoded by the alt1-5 gene cluster. Despite its known bioactivity, the stereochemical configuration of the three stereogenic centers in its polyketide backbone has remained unresolved. In this study, we determined the complete stereostructure of alternapyrone using an integrative approach that combines predictive, rule-based stereochemical analysis with experimental validation through total synthesis. The efficient total synthesis enabled the precise assignment of the hypothesized stereochemistry by matching the synthetic product to the natural compound. This comprehensive study conclusively established the absolute configuration of alternapyrone.

Source: Molecules

DOI: 10.3390/molecules30071597

Authors: Hui Zhang, Jiaxuan Feng, Di Wang, Bencan Tang, Chao Xu, Tao Ye

Institutions: Peking University, University of Nottingham Ningbo China

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

Open Access status: gold

Estimated APC paid: $3,258

Funders: National Natural Science Foundation of China, Natural Science Foundation of Guangdong Province