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Literature DB >> 30426646

A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa.

Jan Rinkel¹, Lukas Lauterbach¹, Jeroen S Dickschat¹.

Abstract

A diterpene synthase from Saccharopolyspora spinosa was found to convert geranylgeranyl diphosphate into the new natural products spinodiene A and B, accompanied by 2,7,18-dolabellatriene. The structures and the formation mechanism of the enzyme products were investigated by extensive isotopic labelling experiments, which revealed an unusual branched isomerisation mechanism towards the neutral intermediate 2,7,18-dolabellatriene. A Diels-Alder reaction was used to convert the main diterpene product with its rare conjugated diene moiety into formal sesterterpene alcohols.

Entities: Chemical Species

Keywords: NMR spectroscopy; biosynthesis; enzyme mechanisms; isotopes; terpenes

Year: 2018 PMID： 30426646 DOI： 10.1002/anie.201812216

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

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Cited

6 in total

1. Mechanistic Insights into the Formation of the 6,10-Bicyclic Eunicellane Skeleton by the Bacterial Diterpene Synthase Bnd4.

Authors: Baofu Xu; Dean J Tantillo; Jeffrey D Rudolf
Journal: Angew Chem Int Ed Engl Date: 2021-09-20 Impact factor: 16.823

2. Deceptive Complexity in Formation of Cleistantha-8,12-diene.

Authors: Jin Liang; Amy T Merrill; Croix J Laconsay; Anwei Hou; Qingyu Pu; Jeroen S Dickschat; Dean J Tantillo; Qiang Wang; Reuben J Peters
Journal: Org Lett Date: 2022-04-06 Impact factor: 6.072

3. An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma.

Authors: Keiichi Murai; Lukas Lauterbach; Kazuya Teramoto; Zhiyang Quan; Lena Barra; Tsuyoshi Yamamoto; Kenichi Nonaka; Kazuro Shiomi; Makoto Nishiyama; Tomohisa Kuzuyama; Jeroen S Dickschat
Journal: Angew Chem Int Ed Engl Date: 2019-09-09 Impact factor: 15.336

A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa.

1. Mechanistic Insights into the Formation of the 6,10-Bicyclic Eunicellane Skeleton by the Bacterial Diterpene Synthase Bnd4.

2. Deceptive Complexity in Formation of Cleistantha-8,12-diene.

3. An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma.

4. Diterpene Biosynthesis in Catenulispora acidiphila: On the Mechanism of Catenul-14-en-6-ol Synthase.

5. On the mass spectrometric fragmentations of the bacterial sesterterpenes sestermobaraenes A-C.

6. Mechanism of the Bifunctional Multiple Product Sesterterpene Synthase AcAS from Aspergillus calidoustus.