The Diterpenoid Substrate Analogue 19-nor-GGPP Reveals Pronounced Methyl Group Effects in Diterpene Cyclisations.
Angew Chem Int Ed Engl
; 63(6): e202318375, 2024 02 05.
Article
em En
| MEDLINE
| ID: mdl-38117607
ABSTRACT
The substrate analogue 19-nor-geranylgeranyl diphosphate (19-nor-GGPP) was synthesised and incubated with 20â
diterpene synthases, resulting in the formation of diterpenoids in all cases. A total of 23â
different compounds were isolated from these enzyme reactions and structurally characterised, if possible including the experimental determination of absolute configurations through a stereoselective deuteration approach. In several cases the missing 19-Me group in the substrate analogue resulted in opening of completely new reaction paths towards compounds with novel skeletons. DFT calculations were applied to gain a deeper understanding of these observed methyl group effects in diterpene biosynthesis.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alquil e Aril Transferases
/
Diterpenos
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article