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Issue 1, 2016
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A method for investigating the stereochemical course of terpene cyclisations

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Abstract

Three sesquiterpene cyclases from Streptomyces scabei 87.22, Streptomyces venezuelae ATCC 10712 and Streptomyces clavuligerus ATCC 27064 were characterised and their products were identified as (−)-neomeranol B, (+)-isodauc-8-en-11-ol and (+)-intermedeol, respectively. The stereochemical courses of the terpene cyclisations were investigated by use of various 13C-labelled FPP isotopomers. A quick and easy test was developed that allows to distinguish reprotonations of olefinic double bonds in neutral intermediates from the two stereoheterotopic faces. The method makes use of incubating 13C-FPP isotopomers labelled at the reprotonated carbon in deuterium oxide and subsequent HSQC analysis of the product. A 1,7-cyclisation towards (+)-isodauc-8-en-11-ol was followed by use of (1,7-13C2)FPP. Surprisingly, the (+)-isodauc-8-en-11-ol also accepted (2Z,6E)-FPP resulting in the same product profile as obtained from (2E,6E)-FPP.

Graphical abstract: A method for investigating the stereochemical course of terpene cyclisations

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Supplementary files

Article information


Submitted
25 Sep 2015
Accepted
12 Oct 2015
First published
15 Oct 2015

Org. Biomol. Chem., 2016,14, 158-164
Article type
Paper

A method for investigating the stereochemical course of terpene cyclisations

P. Rabe, J. Rinkel, T. A. Klapschinski, L. Barra and J. S. Dickschat, Org. Biomol. Chem., 2016, 14, 158
DOI: 10.1039/C5OB01998B

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