54632-04-1Relevant articles and documents
Enzymatic Addition of Alcohols to Terpenes by Squalene Hopene Cyclase Variants
Kühnel, Lisa C.,Nestl, Bettina M.,Hauer, Bernhard
, p. 2222 - 2225 (2017/10/09)
Squalene–hopene cyclases (SHCs) catalyze the polycyclization of squalene into a mixture of hopene and hopanol. Recently, amino-acid residues lining the catalytic cavity of the SHC from Alicyclobacillus acidocaldarius were replaced by small and large hydrophobic amino acids. The alteration of leucine 607 to phenylalanine resulted in increased enzymatic activity towards the formation of an intermolecular farnesyl–farnesyl ether product from farnesol. Furthermore, the addition of small-chain alcohols acting as nucleophiles led to the formation of non-natural ether-linked terpenoids and, thus, to significant alteration of the product pattern relative to that obtained with the wild type. It is proposed that the mutation of leucine at position 607 may facilitate premature quenching of the intermediate by small alcohol nucleophiles. This mutagenesis-based study opens the field for further intermolecular bond-forming reactions and the generation of non-natural products.
Total synthesis of bioactive drimane-epoxyquinol hybrid natural products: Macrophorin A, 4′-oxomacrophorin A, and 1′-epi-craterellin A
Garai, Sumanta,Mehta, Goverdhan
, p. 6252 - 6256 (2014/12/10)
Total synthesis of novel hybrid natural products, merosesquiterpenoids macrophorin A, 4′-oxomacrophorin A, and 1′-epi-craterellin A has been accomplished following a general strategy based on a sacrificial Diels-Alder-retroDiels-Alder approach to control regio- and stereoselectivity.
New access to sesquiterpene hydroquinones: Synthesis of (+)-ent-chromazonarol
Villamizar, Jose,Plata, Federico,Canudas, Nieves,Tropper, Eleonora,Fuentes, Juan,Orcajo, Angel
, p. 311 - 320 (2007/10/03)
A facile access to optically active (+)-ent-chromazonarol ent-1, isolated from the sponge Disidea pallescens, is reported from commercially available (+)-manool 4. Copyright Taylor & Francis LLC.