Synthesis of 2,5‐Disubstituted Pyrrolidine Alkaloids via A One‐Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts,ChemCatChem

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Synthesis of 2,5‐Disubstituted Pyrrolidine Alkaloids via A One‐Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts
ChemCatChem ( IF 3.8 ) Pub Date : 2018-09-20 , DOI: 10.1002/cctc.201801166
Bruna Z. Costa _{1,

2} , James L. Galman ₁ , Iustina Slabu ₁ , Scott P. France ₁ , Anita J. Marsaioli ₂ , Nicholas J. Turner ₁

Affiliation

A multi‐enzymatic cascade process involving transaminases (TAs) and reductive aminases (RedAms) to produce enantiomerically pure 2,5‐disubstituted pyrrolidine alkaloids from their respective 1,4‐diketones is reported. Several TAs were screened and the best results for diketone monoamination were obtained with an R‐selective TA from Mycobacterium chlorophenicum and with an S‐selective TA from Bacillus megaterium. Pyrroline reduction was best performed by a reductive aminase from Ajellomyces dermatitidis (AdRedAm). Finally, a biocatalytic one‐pot cascade was implemented using the aforementioned enzymes and a variety of 2‐methyl‐5‐alkylpyrrolidines were produced with high (>99 %) conversion, diastereomeric and enantiomeric excess values.

中文翻译：

使用转氨酶和还原胺酶生物催化剂通过一锅级联反应合成2,5-二取代的吡咯烷生物碱

据报道，涉及一个多酶级联过程，涉及转氨酶（TAs）和还原性氨基酶（RedAms），从它们各自的1,4-二酮生产对映体纯的2,5-二取代的吡咯烷生物碱。筛选了几个TA，并用来自氯酚分枝杆菌的R选择性TA和巨大芽孢杆菌的S选择性TA获得了二酮单胺化的最佳结果。吡咯啉还原最好用皮肤Ajellomyces dermatitidis（AdRedAm）。最后，使用上述酶实施了生物催化一锅级联反应，并制得了各种具有高（> 99％）转化率，非对映异构体和对映异构体过量值的2-甲基-5-烷基吡咯烷酮。

更新日期：2018-09-20

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