Process for the stereoselective enzymatic reduction of keto...

Details Process for the stereoselective enzymatic reduction of keto... Process for the stereoselective enzymatic reduction of keto...

C - Chemistry, Metallurgy

12

P

C12P 7/02 (2006.01) C12P 7/24 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2753634

The invention relates to a method for stereo selectively, in particular enantioselectively, and enzymatically reducing keto compounds to the corresponding chiral hydroxy compounds, wherein the keto compounds are reduced using an enantioselective, NADH-specific oxidoreductase, wherein in order to reduce the keto compounds, a polypeptide is used that has an R-ADH signature H-[P; A]-[I; A; Q; V; L]-[G; K]-R at position 204-208 and the following further structural characteristics in the entirety thereof: (i) an N-terminal Rossmann fold GxxxGxG, (ii) a NAG motif at position 87, (iii) a catalytic triad comprising S 139, Y 152, and K 156, (iv) a negatively charged amino acid group at position 37, (v) two C-terminal motifs in the dimerization domain [A; S]-S-F and [V; I]-DG-[G; A]-Y-[T; C; L]-[A; T; S]-[Q; V; R; L; P], (vi) Val or Leu at position 159 (4 places down from K 156), (vii) Asn at position 178, and (viii) a proline group at position 188.

Dans le cas d'un procédé de réduction enzymatique stéréosélective, en particulier énantiosélective, de composés céto en les composés hydroxy chiraux correspondants, suivant lequel les composés céto sont réduits par une oxydoréductase spécifique de NADH, énantiosélective, on utilise pour la réduction des composés céto un polypeptide, lequel présente une signature R-ADH H-[P ; A]-[I ; A ; Q ; V ; L]-[G ; K]-R en position 204-208 et les autres caractéristiques structurales suivantes dans son ensemble : (i) un pli de Rossmann N-terminal GxxxGxG, (ii) un motif NAG en position 87, (iii) une triade catalytique se composant de S 139, Y 152 et K 156, (iv) un reste d'acide aminé chargé négativement en position 37, (v) deux motifs C-terminaux dans le domaine de dimérisation [A ; S]-S-F et [V ; I]-DG-[G ; A]-Y-[T ; C ; L]-[A ; T ; S]-[Q ; V ; R ; L ; P], (vi) Val ou Leu en position 159 (4 positions vers le bas du K 156), (vii) Asn en position 178, et (viii) un reste proline en position 188.

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