73908-30-2Relevant academic research and scientific papers
Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH
Mikleu?evi?, Ana,Primo?i?, Ines,Hrenar, Tomica,Salopek-Sondi, Branka,Tang, Lixia,Elenkov, Maja Majeri?
, p. 930 - 935 (2016/09/13)
Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.
The synthesis of two potent β-3 adrenergic receptor agonists
Bradley, Paul A.,Lecouturier, Yann C.,Noeureuil, Pierre,Patel, Bhairavi,Wheeler, Simon,Carroll, Robert J.,Moore, Robert,Snow, Jonathan
, p. 1326 - 1336 (2011/09/20)
This contribution describes the initial preparation of two potent β-3 receptor agonists 1 and 2. Subsequent scale up of these two compounds was required for further evaluation and proceeded via a common key amine intermediate 24. Synthesis of this key intermediate by way of a Ritter reaction was a vital step in the sequence. Enantioselective Noyori hydrogenation reactions gave access to the chiral epoxides necessary to make the target compounds. Chemistry was developed for the selective dehalogenation of the 2-chloropyridyl group in the presence of a sensitive isoxazole unit to provide access to 1.
DNA-based hydrolytic kinetic resolution of epoxides
Dijk, Ewold W.,Feringa, Ben L.,Roelfes, Gerard
experimental part, p. 2374 - 2377 (2009/04/11)
DNA-bound copper(II) complexes serve as catalysts for the hydrolytic kinetic resolution of 2-pyridyloxiranes in water. Selectivity factors of up to 2.7 were achieved, indicating a chirality transfer of DNA to epoxides via a coordinated metal ion.
Bioconversion of substituted styrenes to the corresponding enantiomerically pure epoxides by a recombinant Escherichia coli strain
Bernasconi, Silvana,Orsini, Fulvia,Sello, Guido,Colmegna, Andrea,Galli, Enrica,Bestetti, Giuseppina
, p. 9157 - 9161 (2007/10/03)
Enantiomerically pure epoxides are produced by bioconversion of the corresponding styrenes using a recombinant Escherichia coli strain containing the styrene monooxygenase gene cloned from Pseudomonas fluorescens ST. Different procedures were used to opti
