20296-29-1Relevant articles and documents
1,1′-Binaphthyl-2,2′-diyl phosphoroselenoyl chloride as a chiral molecular tool for the preparation of enantiomerically pure alcohols and amines
Murai, Toshiaki,Matsuoka, Daichi,Morishita, Ken
, p. 4584 - 4585 (2006)
Enantiomerically pure phosphoroselenoyl chloride bearing a binaphthyl group was synthesized. This phosphoroselenoyl chloride was used to discriminate and resolve simple secondary alcohols. Stereospecific conversions of diastereomerically pure phosphoroselenoic acid esters, obtained by reaction of the chloride with simple secondary alcohols, to enantiomerically pure alcohols and amines were also achieved. Copyright
Selectivity-enhancement in enantioselective hydrolysis of sec-alkyl sulfates by an alkylsulfatase from Rhodococcus ruber DSM 44541
Pogorevc, Mateja,Strauss, Ulrike T.,Riermeier, Thomas,Faber, Kurt
, p. 1443 - 1447 (2002)
The Enantioselectivity of the biohydrolysis of sec-alkyl sulfate esters using a bacterial alkylsulfatase from Rhodococcus ruber DSM 44541 was dramatically enhanced in presence of additives ('enhancers') such as carbohydrates, polyethylene glycol, detergents, metal ions and through enzyme immobilization. In presence of iron, the E value for the kinetic resolution of (±)-3- and (±)-4-octyl sulfate was improved from E=3.9 to ≥200 and E=1.1 to 10, respectively.
Enzymatic synthesis of (S)-(-)-1-(2-thienyl)propyl acetate
Kang,Jeon,Yamaguchi,Kim,Ko
, p. 2139 - 2142 (1995)
(±)-1-(2-thienyl)propyl acetate was resolved by PCL (Pseudomonas cepacia lipase) catalyzed hydrolysis to afford (S)-(-)-1-(2-thienyl)propyl acetate in >99% e.e. (S)-(-)-1-(2-thienyl)propyl acetate thus obtained was transformed to (S)-(+)-3-octanol, the alarm pheromone of ants, Crematogaster castanea and liengmei.
Organic-inorganic nanocrystal reductase to promote green asymmetric synthesis
Koesoema, Afifa Ayu,Matsuda, Tomoko,Tsriwong, Kotchakorn
, p. 30953 - 30960 (2020/09/11)
An acetophenone reductase from Geotrichum candidum (GcAPRD) was immobilized by the organic-inorganic nanocrystal method. The GcAPRD nanocrystal presented improved stability and recyclability compared with those of the free GcAPRD. Moreover, the GcAPRD nanocrystal reduced broad kinds of ketones with excellent enantioselectivities to produce beneficial chiral alcohols such as (S)-1-(3′,4′-dichlorophenyl)ethanol with >99% yield and >99% ee. The robust and versatile properties of the GcAPRD nanocrystal demonstrated an approach to promote green asymmetric synthesis and sustainable chemistry. This journal is
Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
Demming, Rebecca M.,Hammer, Stephan C.,Nestl, Bettina M.,Gergel, Sebastian,Fademrecht, Silvia,Pleiss, Jürgen,Hauer, Bernhard
supporting information, p. 173 - 177 (2018/12/11)
The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long-standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.
Biocatalytic Racemization Employing TeSADH: Substrate Scope and Organic Solvent Compatibility for Dynamic Kinetic Resolution
Pop?oński, Jaros?aw,Reiter, Tamara,Kroutil, Wolfgang
, p. 763 - 768 (2018/02/27)
Racemization in combination with a kinetic resolution is the base for a dynamic kinetic resolution (DKR). Biocatalytic racemization was successfully performed for a broad scope of sec-alcohols by employing a single alcohol dehydrogenase (ADH) variant from Thermoanaerobacter pseudoethanolicus (formerly T. ethanolicus; TeSADH W110A I86A C295A). The catalyst employed as a lyophilized whole cell preparation or cell free extract, which tolerated various non-water miscible organic solvents under micro-aqueous or two-phase conditions, whereby cyclohexane and n-hexane suited best. Various concepts for combining the enzymatic racemization with an enzymatic kinetic resolution to achieve overall a bis-enzymatic DKR were evaluated. A proof of concept showed a successful DKR with racemization in aqueous phase combined with acylation in the organic phase.