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.
Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid
Kimura, Mayumi,Kuboki, Atsuhito,Sugai, Takeshi
, p. 1059 - 1068 (2007/10/03)
Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.