A method for investigating the stereochemical course of terpene cyclisations
| Autor: | Jan Rinkel, Lena Barra, Tim A. Klapschinski, Jeroen S. Dickschat, Patrick Rabe |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Streptomyces venezuelae
Double bond Stereochemistry Molecular Conformation Streptomyces clavuligerus Stereoisomerism 010402 general chemistry Sesquiterpene 01 natural sciences Biochemistry Streptomyces Isotopomers Terpene chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry chemistry.chemical_classification biology 010405 organic chemistry Chemistry Terpenes Organic Chemistry biology.organism_classification 0104 chemical sciences Cyclization ddc:540 |
| Popis: | 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 (13)C-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 (13)C-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-(13)C2)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. published |
| Databáze: | OpenAIRE |
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