Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation
Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation
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DOI：
10.1002/adsc.201600934
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发表时间：
2017-05-02
影响因子：
5.4
通讯作者：
Zaparucha, Anne
中科院分区：
文献类型：
--
作者：
Baud, Damien;Peruch, Olivier;Zaparucha, Anne
氨基醇是天然和合成分子中非常常见的结构基序。从L-赖氨酸和羟基-L-赖氨酸开始，提出了β-和γ-氨基醇的简单生物催化合成。由α-酮酸依赖性加氧酶催化的非对映选择性C-H氧化，随后由磷酸吡哆醛依赖性脱羧酶裂解相应手性羟基氨基酸的羧酸部分，从而能够以中度至完全转化形成目标氨基醇。以优异的产率和立体选择性小规模获得了四种 β- 和 γ- 氨基醇。
Amino alcohols are a very common structural motif in natural and synthetic molecules. Starting from l-lysine and hydroxy-l-lysine, a straightforward biocatalytic synthesis of beta- and gamma-amino alcohols is presented. Diastereoselective C-H oxidation catalyzed by an alpha-keto acid-dependent oxygenase followed by cleavage of the carboxylic acid moiety of the corresponding chiral hydroxy amino acid by a pyridoxal phosphate-dependent decarboxylase enabled the formation of the target amino alcohols with moderate to complete conversions. Four beta- and gamma-amino alcohols were obtained on a small scale in excellent yields and stereoselectivities.