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Application of Threonine Aldolases for the Asymmetric Synthesis of ?-Quaternary ?-Amino Acids.

ABSTRACT: We report the synthesis of diverse ?-hydroxy-?,?-dialkyl-?-amino acids with perfect stereoselectivity for the ?-quaternary center through the action of l- and d-specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80?% were obtained. In the case of d-selective threonine aldolase from Pseudomonas sp., generally higher diastereoselectivities were observed. The applicability of the protocol was demonstrated by performing enzymatic reactions on preparative scale. Using the d-threonine aldolase from Pseudomonas sp., (2R,3S)-2-amino-3-(2-fluorophenyl)-3-hydroxy-2-methylpropanoic acid was generated in preparative amounts in one step with a diastereomeric ratio >100 favoring the syn-product. A Birch-type reduction enabled the reductive removal of the ?-hydroxy group from (2S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid to generate enantiopure l-?-methyl-phenylalanine via a two-step chemo-enzymatic transformation.

SUBMITTER: Blesl J 

PROVIDER: S-EPMC6485451 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids.

Blesl Julia J   Trobe Melanie M   Anderl Felix F   Breinbauer Rolf R   Strohmeier Gernot A GA   Fesko Kateryna K  

ChemCatChem 20180704 16

We report the synthesis of diverse β-hydroxy-α,α-dialkyl-α-amino acids with perfect stereoselectivity for the α-quaternary center through the action of l- and d-specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80 % were obtained. In the case of d-selective threonine aldolase from <i>Pseudomonas</i> sp., generally higher diastereoselectivities were observed. The applicability of the protocol was demonstrated by pe  ...[more]

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