59092-94-3Relevant articles and documents
Characterization of phenolic compounds from Rhododendron alutaceum
Li, Hai-Zhou,Song, He-Jiao,Li, Hong-Mei,Pan, Yu-Yin,Li, Rong-Tao
, p. 1887 - 1893 (2012)
A new phenolic glycoside, 3′-keto rhododendrin (1) and a new sesquilignan, alutaceuol (2), together with twelve known phenolic compounds, were isolated from the leaves of Rhododendron alutaceum. Their structures were elucidated by extensive spectroscopic data analysis and comparison with literature values. In addition, the detailed analysis of 2D NMR data led us to conclude that the chemical shifts of dihydrobuddlenol B (5) need to be revised.
Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus
Hamdan, Samir M.,Musa, Musa M.,Nafiu, Sodiq A.,Takahashi, Etsuko,Takahashi, Masateru
, (2020/07/24)
We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.
Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation
Musa, Musa M.,Bsharat, Odey,Karume, Ibrahim,Vieille, Claire,Takahashi, Masateru,Hamdan, Samir M.
, p. 798 - 805 (2018/02/21)
Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.
Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues
Kitayama, Takashi,Isomori, Sachiko,Nakamura, Kaoru
, p. 621 - 627 (2013/07/19)
The achiral zingerone 1, readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp. (Meito QLM) and vinyl acetate in i-Pr2O or hexane at 35 C within 1 h gave the alcohol (S)-2 and the acetate (R)-9 with high enantioselectivity without producing acetylated by-products. Since optically active (S)-2 and (R)-9 were obtained through lipase-catalyzed transesterification, other enantiomerically pure novel compounds could all be synthesized.