90458-95-0Relevant articles and documents
FIRST STEREOSPECIFIC SYNTHESIS OF E-γ-BISABOLENE. A METHOD FOR THE CONCURRENT GENERATION OF A RING AND A TETRASUBSTITUTED EXOCYCLIC DOUBLE BOND.
Corey, E. J.,Seibel, William L.
, p. 905 - 908 (1986)
A short stereospecific synthesis of E-γ-bisabolene (1) from an acyclic acetylenic precursor (either 2 or 6) is described.
Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum
Rinkel, Jan,Dickschat, Jeroen S.
, p. 789 - 794 (2019/04/17)
A newly identified bacterial (Z)-γ-bisabolene synthase was used for investigating the cyclisation mechanism of the sesquiterpene. Since the stereoinformation of both chiral putative intermediates, nerolidyl diphosphate (NPP) and the bisabolyl cation, is lost during formation of the achiral product, the intriguing question of their absolute configurations was addressed by incubating both enantiomers of NPP with the recombinant enzyme, which resolved in an exclusive cyclisation of (R)-NPP, while (S)-NPP that is non-natural to the (Z)-γ-bisabolene synthase was specifically converted into (E)-β-farnesene. A hypothetical enzyme mechanistic model that explains these observations is presented.
METHOD FOR THE PRODUCTION OF ALPHA-BISABOLOL FROM NEROLIDOL
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Page/Page column 9, (2008/06/13)
The invention relates to a method for the production of alpha-bisabolol, consiting of the following step: nerolidol is reacted with a mixture of ketone, sulfonic acid and perchloric acid.