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Abstract
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 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 β-hydroxy group from (2S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid to generate enantiopure l-α-methyl-phenylalanine via a two-step chemo-enzymatic transformation.
Original language | English |
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Pages (from-to) | 3453-3458 |
Number of pages | 6 |
Journal | ChemCatChem |
Volume | 10 |
Issue number | 16 |
DOIs | |
Publication status | Published - 21 Aug 2018 |
Keywords
- Amino acids
- Asymmetric catalysis
- Enzyme catalysis
- Quaternary stereogenic centers
- Threonine aldolases
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Fields of Expertise
- Human- & Biotechnology
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Dive into the research topics of 'Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids'. Together they form a unique fingerprint.Projects
- 1 Finished
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EU - CHEM 21 - Chemical Manufacturing Methods for the 21st Century Pharmaceutical Industries
Breinbauer, R. & Camattari, A.
1/12/12 → 30/11/16
Project: Research project