Emerindanols A and B: Two Bipolyhydroindenol Sesterterpenes with 5/6–6/5 Coupled Ring System Discovered by Genome Mining

Genome mining of Emericella sp. XL-029 achieved a new type E sesterterpene synthase, EmES, which affored a novel bipolyhydroindenol sesterterpene, emerindanol A. Heterologous coexpression with the upstream P450 oxidase revealed C-4 hydroxylated product, emerindanol B. Notably, emerindanols A and B r...

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Published inOrganic letters Vol. 26; no. 21; pp. 4475 - 4479
Main Authors Liu, Shuzhi, Wang, Wenjing, Liu, Qingpei, Yao, Ming, Liao, Liangxiu, Gao, Shuaibiao, Yu, Yi, Yang, Xiaolong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Emericella - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Sesterterpenes - chemistry
GENE
TERPENE SYNTHASES
REVEALS
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Summary:Genome mining of Emericella sp. XL-029 achieved a new type E sesterterpene synthase, EmES, which affored a novel bipolyhydroindenol sesterterpene, emerindanol A. Heterologous coexpression with the upstream P450 oxidase revealed C-4 hydroxylated product, emerindanol B. Notably, emerindanols A and B represented the first sesterterpenes featuring a unique 5/6–6/5 coupled ring system. EmES was postulated to initiate through C1–IV–V pathway and convert the fused ring intermediate into the final coupled ring product through a spiro skeleton.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01272