Total Synthesis and Stereochemical Assignment of Alternapyrone

Hui Zhang; Jiaxuan Feng; Di Wang; Bencan Tang; Chao Xu; Tao Ye

doi:10.3390/molecules30071597

Total Synthesis and Stereochemical Assignment of Alternapyrone

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

Department of Chemical and Environmental Engineering

Research output: Journal Publication › Article › peer-review

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.

Original language	English
Article number	1597
Journal	Molecules
Volume	30
Issue number	7
DOIs	https://doi.org/10.3390/molecules30071597
Publication status	Published - Apr 2025

Keywords

absolute configuration
natural products
prediction
total synthesis

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules30071597

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title = "Total Synthesis and Stereochemical Assignment of Alternapyrone",

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.",

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AU - Zhang, Hui

AU - Feng, Jiaxuan

AU - Wang, Di

AU - Tang, Bencan

AU - Xu, Chao

AU - Ye, Tao

PY - 2025/4

Y1 - 2025/4

N2 - 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.

AB - 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.

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KW - prediction

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Total Synthesis and Stereochemical Assignment of Alternapyrone

Abstract

Keywords

ASJC Scopus subject areas

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