Efficient Synthesis of (S)‑1-Boc-3-aminopiperidine
in a Continuous Flow System Using ω‑Transaminase-Immobilized
Amino-Ethylenediamine-Modified Epoxide Supports
Posted on 2022-04-15 - 17:10
We
developed a continuous flow system using ω-transaminase
covalently immobilized on an epoxy resin modified with ethylenediamine
(EDA) to synthesize (S)-1-Boc-3-aminopiperidine,
which is a key intermediate for several novel inhibitors. A second
functional group (−NH3+) 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)-1-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)-1-Boc-3-aminopiperidine.
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Wang, Xiangxiang; Xie, Youyu; Wang, Zhicai; Zhang, Ke; Wang, Hualei; Wei, Dongzhi (2022). Efficient Synthesis of (S)‑1-Boc-3-aminopiperidine
in a Continuous Flow System Using ω‑Transaminase-Immobilized
Amino-Ethylenediamine-Modified Epoxide Supports. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.1c00217