515-69-5Relevant articles and documents
Synthesis method of 3-methyl-2-butene-1-geranoil formate
-
Paragraph 0043-0050, (2018/07/06)
The invention belongs to the technical field of chemical synthesis and particularly relates to a synthesis method of 3-methyl-2-butene-1-geranoil formate. According to the synthesis method of the 3-methyl-2-butene-1-geranoil formate and on the basis of the existing technical process, sodium hydrogen sulfite serves as a catalyst, the yield of a 3-methyl-2-butene-1-geranoil formate product is further increased, more preferably, reaction is conducted under the existence of ionic liquid, the reaction time is effectively increased besides the yield of the products is effectively increased, and higher product yield can be obtained within shorter time.
Enantioselective microbial synthesis of the indigenous natural product (-)-α-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita)
Son, Young-Jin,Kwon, Moonhyuk,Ro, Dae-Kyun,Kim, Soo-Un
, p. 239 - 248 (2015/03/03)
(-)-α-Bisabolol, a sesquiterpene alcohol, is a major ingredient in the essential oil of chamomile (Matricaria recutita) and is used in many health products. The current supply of (-)-α-bisabolol is mainly dependent on the Brazilian candeia tree (Eremanthus erythropappus) by distillation or by chemical synthesis. However, the distillation method using the candeia tree is not sustainable, and chemical synthesis suffers from impurities arising from undesirable α-bisabolol isomers. Therefore enzymatic synthesis of (-)-α-bisabolol is a viable alternative. In the present study, a cDNA encoding (-)-α-bisabolol synthase (MrBBS) was identified from chamomile and used for enantioselective (-)-α-bisabolol synthesis in yeast. Chamomile MrBBS was identified by Illumina and 454 sequencing, followed by activity screening in yeast. When MrBBS was expressed in yeast, 8mg of α-bisabolol was synthesized de novo per litre of culture. The structure of purified α-bisabolol was elucidated as (S,S)- α-bisabolol [or (-)-α-bisabolol]. Although MrBBS possesses a putative chloroplast-targeting peptide, it was localized in the cytosol, and a deletion of its N-terminal 23 amino acids significantly reduced its stability and activity. Recombinant MrBBS showed kinetic properties comparable with those of other sesquiterpene synthases. These data provide compelling evidence that chamomile MrBBS synthesizes enantiopure (-)-α-bisabolol as a single sesquiterpene product, opening a biotechnological opportunity to produce (-)-α-bisabolol.
Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesvl diohosohate
Faraldos, Juan A.,O'Maille, Paul E.,Dellas, Nikki,Noel, Joseph P.,Coates, Robert M.
experimental part, p. 4281 - 4289 (2010/05/15)
We report the structures and stereochemistry of seven bisabolyl-derived sesquiterpenes arising from an unprecedented 1,6-cyclization (cisoid pathway) efficiently catalyzed by tobacco 5-epi-aristolochene synthase (TEAS). The use of (2Z,6E)-farnesyl diphosphate as an alternate substrate for recombinant TEAS resulted in a robust enzymatic cyclization to an array of products derived exclusively (≥99.5%) from the cisoid pathway, whereas these same products account for ca. 2.5% of the total hydrocarbons obtained using (2E,6E)-farnesyl diphosphate. Chromatographic fractionations of extracts from preparative incubations with the 2Z,6E substrate afforded, in addition to the acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (3.6%), five cyclic sesquiterpene hydrocarbons and two cyclic sesquiterpene alcohols: (+)-2-epiprezizaene (44%), (-)-α-cedrene (21.5%), (R)-(-)-β-curcumene (15.5%), R-acoradiene (3.9%), 4-epi-α-acoradiene (1.3%), and equal amounts of α-bisabolol (1.8%) and epi-R-bisalolol (1.8%). The structures, stereochemistry, and enantiopurities were established by comprehensive spectroscopic analyses, optical rotations, chemical correlations with known sesquiterpenes, comparisons with literature data, and GC analyses. The major product, (+)-2-epi-prezizaene, is structurally related to the naturally occurring tricyclic alcohol, jinkohol (2-epi-prezizaan-7 β-ol). Cisoid cyclization pathways are proposed by which all five sesquiterpene hydrocarbons are derived from a common (7R)-β-bisabolyl+/pyrophosphate - ion pair intermediate. The implications of the cisoid catalytic activity of TEAS are discussed.
