Stereoselectivity of an ω-transaminase-mediated amination of 1,3-dihydroxy-1-phenylpropane-2-one

The stereoselectivity of a recently isolated ω-transaminase from Chromobacterium violaceum in the amination of 1,3-dihydroxy-1-phenylpropan-2-one has been determined. The enzyme is not enantioselective towards a racemic mixture of 1,3-dihydroxy-1-phenylpropan-2-one but is highly stereoselective forming (2S)-2-amino-1-phenyl-1,3-propanediols in >99% ee.

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(2S,3R) Ethyl 3-hydroxy-2-(4-nitrophenylsulfonyloxy)-3-phenylpropanoateC17H17NO8SDe ⩾ 70% [(2R,3R)-diastereoisomer present][α]D24=-42.5 (c 3.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3R)

(2R,3R) Ethyl 2-azido-3-hydroxy-3-phenylpropanoateC11H13N3O3De ⩾ 70% [(2S,3R)-diastereoisomer present][α]D24=+9.4 (c 11.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R)

(1R,2S)-2-Amino-1-phenyl-1,3-propanediolC9H13NO2De ⩾ 70% [(1R,2R)-diastereoisomer present via asymmetric synthesis][α]D20=-14.9 (c 2.0, MeOH)Source of chirality: asymmetric synthesis and biocatalysisAbsolute configuration: (1R,2S)

(1S,2S)-2-Acetamido-1-phenylpropane-1,3-diyl diacetateC15H19NO5Ee ⩾ 98% (derivative of commercial sample)[α]D20=+47.1 (c 2.0, CHCl3)Source of chirality: derivative of commercial sample and biocatalysisAbsolute configuration: (1S,2S)

(1R,2R)-2-Acetamido-1-phenylpropane-1,3-diyl diacetateC15H19NO5Ee ⩾ 98% (derivative of commercial sample)[α]D20=-61.1 (c 2.0, CHCl3)Source of chirality: derivative of commercial sampleAbsolute configuration: (1R,2R)

(1R,2S)-2-Acetamido-1-phenylpropane-1,3-diyl diacetateC15H19NO5De ⩾ 70% [(1R,2R)-diastereoisomer present via asymmetric synthesis][α]D20=-19.4 (c 1.0, CHCl3)Source of chirality: asymmetric synthesis and biocatalysisAbsolute configuration: (1R,2S)