Premium
Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases
Author(s) -
Citron Christian A.,
Rabe Patrick,
Barra Lena,
Nakano Chiaki,
Hoshino Tsutomu,
Dickschat Jeroen S.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403002
Subject(s) - chemistry , labelling , isotopomers , deuterium , reagent , organic chemistry , chemical synthesis , acetone , terpene , ethyl acetoacetate , stereochemistry , biochemistry , catalysis , physics , quantum mechanics , molecule , in vitro
A flexible, efficient and robust method for the synthesis of isotopically labelled oligoprenyl diphosphates was developed. The method makes use of just a few building blocks (acetone, triethyl phosphonoacetate, and ethyl acetoacetate) from which several isotopomers with deuterium or 13 C‐labelling are commercially available or can be easily obtained by synthesis. Besides these building blocks, a few deuterated reagents were used for the introduction of deuterium labelling. Furthermore, the synthesis of [14‐ 2 H]geranylgeranyl diphosphate is reported. The material was used for a stereochemical analysis of the cyclisation reaction catalysed by tuberculosinyl diphosphate synthase from Mycobacterium tuberculosis .