147028-56-6Relevant academic research and scientific papers
A stereodivergent approach to substituted 4-hydroxypiperidines
Vink, Mandy K. S.,Schortinghuis, Christien A.,Luten, Jordy,Van Maarseveen, Jan H.,Schoemaker, Hans E.,Hiemstra, Henk,Rutjes, Floris P. J. T.
, p. 7869 - 7871 (2007/10/03)
A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.
An enzyme library approach to biocatalysis: Development of nitrilases for enantioselective production of carboxylic acid derivatives
DeSantis, Grace,Zhu, Zuolin,Greenberg, William A.,Wong, Kelvin,Chaplin, Jenny,Hanson, Sarah R.,Farwell, Bob,Nicholson, Lawrence W.,Rand, Cynthia L.,Weiner, David P.,Robertson, Dan E.,Burk, Mark J.
, p. 9024 - 9025 (2007/10/03)
The discovery, from Nature, of a large and diverse set of nitrilases is reported. The utility of this nitrilase library for identifying enzymes that catalyze efficient production of valuable hydroxy carboxylic acid derivatives is demonstrated. Unprecedented enantioselectivity and substrate scope are highlighted for three newly discovered and distinct nitrilases. For example, a wide array of (R)-mandelic acid derivatives and analogues were produced with high rates, yields, and enantiomeric excesses (95-99% ee). We also have found nitrilases that provide direct access to (S)-phenyllactic acid and other aryllactic acid derivatives, again with high yields and enantioselectivities. Finally, different nitrilases have been discovered that catalyze enantiotopic hydrolysis of 3-hydroxyglutaronitrile to afford either enantiomer of 4-cyano-3-hydroxybutyric acid with high enantiomeric excesses (>95% ee). The first enzymes are reported that effect this transformation to furnish the (R)-4-cyano-3-hydroxybutyric acid which is a precursor to the blockbuster drug Lipitor. Copyright
Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids
Maddrell, Samuel J.,Turner, Nicholas J.,Kerridge, Alison,Willetts, Andrew J.,Crosby, John
, p. 6001 - 6004 (2007/10/03)
(R)-4-Hydroxy-5-cyanopentene (-)-9, a known precursor of the protected lactone moiety of the mevinic acids 1, has been prepared in 9 steps from (S)-3-(benzyloxy)-4-cyanobutanoic acid 5 (88% e.e.) which was obtained by the asymmetric 2 step hydrolysis of 3-benzyloxyglutaronitrile 4 involving the successive activity of a nitrile hydratase and an amidase enzyme.
Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst
Beard, Timothy,Cohen, Mark A.,Parratt, Julian S.,Turner, Nicholas J.,Crosby, John,Moilliet, Jock
, p. 1085 - 1104 (2007/10/02)
An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.
Microbial Hydrolysis of 3-Substituted Glutaronitriles
Kakeya, Hideaki,Sakai, Naoko,Sano, Akio,Yokoyama, Masahiro,Sugai, Takeshi,et al.
, p. 1823 - 1824 (2007/10/02)
Rhodococcus butanica ATCC 21197 preferentially hydrolyzed pro-S cyano group of 3-substituted glutaronitriles with an aromatic ring.A product with high e.e. (>99 percent) was obtained from 3-benzoyloxy derivative.
