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Literature DB >> 29953712

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids.

Clara Oberhauser¹, Vanessa Harms¹, Katja Seidel¹, Benjamin Schröder¹, Kimia Ekramzadeh², Sascha Beutel², Sven Winkler³, Lukas Lauterbach⁴, Jeroen S Dickschat⁴, Andreas Kirschning¹.

Abstract

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

Entities: Chemical

Keywords: biocatalysis; farnesyl pyrophosphates; scent compounds; terpene cyclases; terpenoids

Year: 2018 PMID： 29953712 DOI： 10.1002/anie.201805526

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

13 in total

1. Probing the Substrate Promiscuity of Isopentenyl Phosphate Kinase as a Platform for Hemiterpene Analogue Production.

Authors: Sean Lund; Taylor Courtney; Gavin J Williams
Journal: Chembiochem Date: 2019-07-22 Impact factor: 3.164

2. New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections.

Authors: Evgenii V Suslov; Evgenii S Mozhaytsev; Dina V Korchagina; Nikolay I Bormotov; Olga I Yarovaya; Konstantin P Volcho; Olga A Serova; Alexander P Agafonov; Rinat A Maksyutov; Larisa N Shishkina; Nariman F Salakhutdinov
Journal: RSC Med Chem Date: 2020-08-06

3. Using Terpene Synthase Plasticity in Catalysis: On the Enzymatic Conversion of Synthetic Farnesyl Diphosphate Analogues.

Authors: Anwei Hou; Jeroen S Dickschat
Journal: Chemistry Date: 2021-09-29 Impact factor: 5.020

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids.

1. Probing the Substrate Promiscuity of Isopentenyl Phosphate Kinase as a Platform for Hemiterpene Analogue Production.

2. New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections.

3. Using Terpene Synthase Plasticity in Catalysis: On the Enzymatic Conversion of Synthetic Farnesyl Diphosphate Analogues.

4. Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids.

Review 5. Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase.

6. Accelerating Biphasic Biocatalysis through New Process Windows.

Review 7. Germacrene A-A Central Intermediate in Sesquiterpene Biosynthesis.

8. Engineering of Ancestors as a Tool to Elucidate Structure, Mechanism, and Specificity of Extant Terpene Cyclase.

9. Enzymatic Synthesis of Methylated Terpene Analogues Using the Plasticity of Bacterial Terpene Synthases.

Review 10. Current understanding and biotechnological application of the bacterial diterpene synthase CotB2.

Review 5. Synthetic terpenoids in the world of fragrances: Iso E Super® is the showcase.

Review 7. Germacrene A-A Central Intermediate in Sesquiterpene Biosynthesis.

Review 10. Current understanding and biotechnological application of the bacterial diterpene synthase CotB2.

Review 5. Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase.