期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 39, 页码 13999-14005出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602084
关键词
asymmetric synthesis; biocatalysis; C-C coupling; thiamine diphosphate; vitamin B1
资金
- German Research Council DFG [FOR 1296]
The catalytic asymmetric synthesis of chiral 2-hydroxy ketones by using different thiamine diphosphate dependent enzymes, namely benzaldehyde lyase from Pseudomonas fluorescens (PfBAL), a variant of benzoylformate decarboxylase from Pseudomonas putida (PpBFD-L461A), branched-chain 2-keto acid decarboxylase from Lactococcus lactis (LlKdcA) and a variant of pyruvate decarboxylase from Acetobacter pasteurianus (ApPDC-E469G), was studied. Starting with the same set of substrates, substituted benzaldehydes in combination with different aliphatic aldehydes, PfBAL and PpBFD-L461A selectively deliver the (R)-and (S)-2-hydroxy-propiophenone derivatives, respectively. The (R)and (S)-phenylacetylcarbinol (1-hydroxy-1-phenylacetone) derivatives are accessible in a similar way using LlKdcA and ApPDC-E469G, respectively. In many cases excellent stereochemical purities (>98% enantiomeric excess) could be achieved. Hence, the regio- and stereochemistry of the product in the asymmetric aliphatic-aromatic cross-benzoin reaction can be controlled solely by choice of the appropriate enzyme or enzyme variant.
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