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Emerindanols A and B: Two Bipolyhydroindenol Sesterterpenes with 5/6-6/5 Coupled Ring System Discovered by Genome Mining. | LitMetric

AI Article Synopsis

  • Genome mining of sp. XL-029 led to the discovery of a new type E sesterterpene synthase called EmES, which produced a novel compound, emerindanol A.
  • Emerindanol B was identified as a C-4 hydroxylated product through heterologous coexpression with P450 oxidase.
  • Emerindanol A and B are the first sesterterpenes known to have a unique 5/6-6/5 coupled ring system, with a proposed synthesis pathway involving C1-IV-V and a spiro skeleton.

Article Abstract

Genome mining of 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.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c01272DOI Listing

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