945451-09-2Relevant academic research and scientific papers
Investigation of asymmetric alcohol dehydrogenase (ADH) reduction of acetophenone derivatives: Effect of charge density
Naik, Hemantkumar G.,Yeniad, Bahar,Koning, Cor E.,Heise, Andreas
supporting information; experimental part, p. 4961 - 4967 (2012/08/08)
In an effort to study the effect of substituent groups of the substrate on the alcohol dehydrogenase (ADH) reductions of aryl-alkyl ketones, several derivatives of acetophenone have been evaluated against ADHs from Lactobacillus brevis (LB) and Thermoanaerobacter sp. (T). Interestingly, ketones with non-demanding (neutral) para-substituents were reduced to secondary alcohols by these enzymes in enantiomerically pure form whereas those with demanding (ionizable) substituents could not be reduced. The effect of substrate size, their solubility in the reaction medium, electron donating and withdrawing properties of the ligand and also the electronic charge density distribution on the substrate molecules have been studied and discussed in detail. From the results, it is observed that the electronic charge distribution in the substrate molecules is influencing the orientation of the substrate in the active site of the enzyme and hence the ability to reduce the substrate.
Encoded dendrimers with defined chiral composition via 'click' reaction of enantiopure building blocks
Yeniad, Bahar,Naik, Hemantkumar,Amir, Roey J.,Koning, Cor E.,Hawker, Craig J.,Heise, Andreas
supporting information; experimental part, p. 9870 - 9872 (2011/10/11)
Dendrimers with end-groups of defined chiral composition have been prepared from alkyne functional enantio-pure building blocks obtained by selective enzymatic (ADH) ketone reductions using click chemistry. Optical rotation and enantioselective enzymatic
Click-connected ligand scaffolds: macrocyclic chelates for asymmetric hydrogenation
Qing, Zhang,Takacs, James M.
, p. 545 - 548 (2008/09/17)
Click chemistry is used to construct ligand scaffolds for a series of chiral diphosphites. Enantioselectivity as high as 97% ee is obtained using these click ligands in rhodium-catalyzed asymmetric hydrogenation. Control experiments and spectroscopic data suggest that a 16-membered P,P-macrocyclic Rh(1) chelate is formed.
Macromolecular helicity inversion of an optically active helical poly(phenylacetylene) by chemical modification of the side groups
Kobayashi, Shinzo,Morino, Kazuhide,Yashima, Eiji
, p. 2351 - 2353 (2008/02/10)
An optically active helical poly(phenylacetylene) was synthesized by the copolymerization of phenylacetylenes bearing optically active hydroxy or ester groups obtained by the kinetic resolution of a racemic phenylacetylene with lipase; the helix-sense was
