Biocontrolled Formal Inversion or Retention of L-α-Amino Acids to Enantiopure (R)- or (S)-Hydroxyacids

Biocontrolled Formal Inversion or Retention of L-α-Amino Acids to Enantiopure (R)- or (S)-Hydroxyacids
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DOI:
10.1002/chem.201403195
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发表时间:
2014-08-25
影响因子:
4.3
通讯作者:
Kroutil, Wolfgang
Kroutil, Wolfgang
中科院分区:
化学2区
文献类型:
--
作者:
Busto, Eduardo;Richter, Nina;Kroutil, Wolfgang

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通过形式生物催化转化或保留绝对构型将天然L-α-氨基酸和L-正亮氨酸转化为相应的α-羟基酸。一锅转化是通过水介质中同时发生的氧化还原级联实现的。具有脂肪族、芳香族和杂芳香族部分的一组代表性对映体纯 (R)-和 (S)-2-羟基酸以高收率 (67-85%) 和对映体纯形式 (>99% ee) 分离,无需色谱纯化。
Natural L-alpha-amino acids and L-norleucine were transformed to the corresponding alpha-hydroxy acids by formal biocatalytic inversion or retention of absolute configuration. The one-pot transformation was achieved by a concurrent oxidation reduction cascade in aqueous media. A representative panel of enantiopure (R)- and (S)-2-hydroxy acids possessing aliphatic, aromatic and heteroaromatic moieties were isolated in high yield (67-85%) and enantiopure form (>99% ee) without requiring chromatographic purification.