Organic process research & development2022,Vol.26Issue(5) :9.DOI:10.1021/acs.oprd.1c00217

Efficient Synthesis of@-1-Boc-3-aminopiperidine in a Continuous Flow System Using ω-Transaminase-lmmobilized Amino-Ethylenediamine-Modified Epoxide Supports

Xiangxiang Wang Youyu Xie Zhicai Wang
Organic process research & development2022,Vol.26Issue(5) :9.DOI:10.1021/acs.oprd.1c00217

Efficient Synthesis of@-1-Boc-3-aminopiperidine in a Continuous Flow System Using ω-Transaminase-lmmobilized Amino-Ethylenediamine-Modified Epoxide Supports

Xiangxiang Wang 1Youyu Xie 1Zhicai Wang2
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作者信息

  • 1. State Key Laboratory of Bioreactor Engineering,New World Institute of Biotechnology,East China University of Science and Technology,Shanghai 200237,P.R.China
  • 2. State Key Laboratory of Bioreactor Engineering New World Institute of Biotechnology,East China University of Science and Technology,Shanghai 200237,P.R.China
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Abstract

We developed a continuous flow system using ^-transaminase covalently immobilized on an epoxy resin modified with ethylenediamine(EDA)to synthesize(S)-l-Boc-3-aminopiperidine,which is a key intermediate for several novel inhibitors.A second functional group(-NH_3~+)was introduced to rapidly adsorb ω-transaminase,which was further rigidified by multipoint covalent attachment to the modified resin with high binding efficiency(>95%)and activity recovery(75%).The resulting immobilized ω-transaminase was stable with 90% residual activity after 15 reuse cycles.We synthesized(S)-l-Boc-3-aminopiperidine using this continuous flow system,and 95% conversion was obtained within 10 min of residence.The system was continuously operated for 24 h and achieved a space-time yield of 930.73 g·L~(-1)·day~(-1),indicating outstanding reaction efficiency.This efficient continuous bioprocess has potential for large-scale production of(S)-l-Boc-3-aminopiperidine.

Key words

enzyme immobilization/bifunctional supports/transaminases/biocatalysis/flow chemistry

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出版年

2022
Organic process research & development

Organic process research & development

CCR
ISSN:1083-6160
被引量3
参考文献量16
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