7733-91-7Relevant articles and documents
Synthesis of a potential enzyme-specific inhibitor of squalene synthase
Valentijn, A. R. P. M.,Haan, R. de,Hagens, S.,Kant, E. de,Marel, G. A. van der,et al.
, p. 332 - 336 (1995)
A multi-step synthesis of phosphinylphosphonate analogue 12 of the proposed farnesyl-farnesyl-enzyme (FFE) intermediate in the enzymatic conversion of farnesyl pyrophosphate to squalene is described.In addition, evidence is presented of the inhibitory effect of 12 on squalene synthase.
Asymmetric Cation-Olefin Monocyclization by Engineered Squalene–Hopene Cyclases
Aeberli, Natalie,Berweger, Raphael,Bornscheuer, Uwe T.,Buller, Rebecca,Dossenbach, Sandro,Eichenberger, Michael,Eichhorn, Eric,Flachsmann, Felix,Hüppi, Sean,Hortencio, Lucas,Patsch, David,Voirol, Francis,Vollenweider, Sabine
supporting information, p. 26080 - 26086 (2021/09/20)
Squalene–hopene cyclases (SHCs) have great potential for the industrial synthesis of enantiopure cyclic terpenoids. A limitation of SHC catalysis has been the enzymes’ strict (S)-enantioselectivity at the stereocenter formed after the first cyclization step. To gain enantio-complementary access to valuable monocyclic terpenoids, an SHC-wild-type library including 18 novel homologs was set up. A previously not described SHC (AciSHC) was found to synthesize small amounts of monocyclic (R)-γ-dihydroionone from (E/Z)-geranylacetone. Using enzyme and process optimization, the conversion to the desired product was increased to 79 %. Notably, analyzed AciSHC variants could finely differentiate between the geometric geranylacetone isomers: While the (Z)-isomer yielded the desired monocyclic (R)-γ-dihydroionone (>99 % ee), the (E)-isomer was converted to the (S,S)-bicyclic ether (>95 % ee). Applying the knowledge gained from the observed stereodivergent and enantioselective transformations to an additional SHC-substrate pair, access to the complementary (S)-γ-dihydroionone (>99.9 % ee) could be obtained.
Biomimetic syntheses from squalene-like precursors: Synthesis of ent- abudinol B and reassessment of the structure of muzitone
Boone, Matthew A.,Tong, Rongbiao,McDonald, Frank E.,Lense, Sheri,Cao, Rui,Hardcastle, Kenneth I.
supporting information; experimental part, p. 5300 - 5308 (2010/06/17)
We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.
