43210-73-7Relevant articles and documents
β Adrenergic blocking agents. 14. Microbiological reduction of isopropylaminomethyl 2 naphthyl ketone to (R) (-) 2 isopropylamino 1 (2 naphthyl) ethanol and related reductions
Howe,Moore,Rao
, p. 1020 - 1023 (1973)
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Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids
Burgener, Simon,Cortina, Ni?a Socorro,Erb, Tobias J.
supporting information, p. 5526 - 5530 (2020/02/20)
The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine-diphosphate-dependent (ThDP) oxalyl-CoA decarboxylase (OXC)/2-hydroxyacyl-CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl-CoA thioester substrates through the release of the C1-unit formyl-CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C1-extensions of various aldehydes to yield the corresponding 2-hydroxyacyl-CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl-CoA synthetase and a 2-hydroxyacyl-CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable (S)-α-hydroxy acids with enantiomeric excess up to 99 %.
Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy- and (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butanes
Kobayashi, Yuka,Kokubo, Yasushi,Aisaka, Takamitsu,Saigo, Kazuhiko
scheme or table, p. 2536 - 2541 (2009/04/11)
Two enantiopure bis(hydroxyamino) compounds were successfully prepared from dialkyl tartrate by a chiral-pool method and applied as basic resolving agents in the enantioseparation of 2-arylpropanoic acids and arylglycolic acids. (2S,3S)-2,3-Dihydroxy-1,4-bis(hydroxyamino)butane (2S,3S)-1a could moderately recognize the chirality of the 2-arylpropanoic acids, while (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butane (2S,3S)-1b could not due to the low crystallinity of both the corresponding diastereomeric salts. On the other hand, (2S,3S)-1b showed a similar chirality-recognition ability for the arylglycolic acids. The ability of (2S,3S)-1b was different from those generally observed for widely used primary amine-type resolving agents with regard to the relationship between the resolution efficiency and the similarity in the relative molecular length of a resolving agent and a target racemate. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that in the salts (2S,3S)-1a formed a supramolecular sheet, of which the distance was variable to make the resultant dissymmetric space fit to the shape of the target acids, and that (2S,3S)-1b was constructed from a robust supramolecular sheet, consisting of hydrogen-bonding 21 columns, with the participation of the hydroxy group of the arylglycolic acids. These X-ray crystallographic analyses also suggested that for the formation of a supramolecular sheet, the coexistence of two hydroxyamino groups is essential.
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
