Chemoenzymatic Generation of Thio-analogues of δ‑Cadinene, δ‑Cadinol, and a Thio-diquinane Using 8‑Thio-farnesylpyrophosphate
Birk Jäger, Jan Luca Budde, Norman Birke, Maximilian Hauke, Andreas Kirschning
TL;DR
Scientists created thio-analogues of certain terpenoids using a modified farnesylpyrophosphate and observed their distinct odors.
Contribution
The novel synthesis of 8-thio-farnesylpyrophosphate and its biotransformation into thio-terpenoids with unique olfactory properties.
Findings
8-thio-farnesylpyrophosphate was successfully synthesized and used in biotransformations.
Thio-analogues of δ-cadinene and δ-cadinol were produced by Cop4 and Omp7 synthases.
A ketothiol diquinane with a spicy aroma was formed by BcBOT2, differing from natural product pathways.
Abstract
The synthesis of 8-thio-farnesylpyrophosphate is reported, which was subjected to biotransformations with different sesquiterpene synthases. The 9-thio-analogues of δ-cadinene and δ-cadinol were formed by the sesquiterpene synthases Cop4 and Omp7. In contrast, the fungal sesquiterpene synthase BcBOT2 yielded a diquinane terpenoid that contains a keto and thiol group. The formation of the two former “sulfo”-terpenoids can be rationalized by following the route proposed for δ-cadinene and δ-cadinol. The latter can be regarded by the result of a late-stage hydrolysis product during the analogous pathway to presilphiperfolan-8β-ol, the natural product of BcBOT2. The olfactoric analysis of the three “sulfo”-sesuiterpenoids revealed a stale odor for the cadinene derivatives, whereas the ketothiol diquinane exhibits a spicy aroma with a subtle chili note.
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Taxonomy
TopicsPlant biochemistry and biosynthesis · Microbial Natural Products and Biosynthesis · Neurobiology and Insect Physiology Research