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Cascade Biotransformation to Access 3‐Methylpiperidine in Whole Cells
Author(s) -
Borlinghaus Niels,
Weinmann Leonie,
Krimpzer Florian,
Scheller Philipp N.,
AlShameri Ammar,
Lauterbach Lars,
Coquel AnneSophie,
Lattemann Claus,
Hauer Bernhard,
Nestl Bettina M.
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900702
Subject(s) - biotransformation , bioconversion , substrate (aquarium) , chemistry , escherichia coli , bioreactor , biocatalysis , diamine , imine , diamine oxidase , reductase , transformation (genetics) , stereochemistry , combinatorial chemistry , organic chemistry , enzyme , biochemistry , reaction mechanism , catalysis , biology , fermentation , ecology , gene
Abstract Synthesis of 3‐methylpiperidine from 1,5‐diamino‐2‐methylpentane in preparative scale is reported by using recombinant Escherichia coli cells expressing a variant of the diamine oxidase from Rhodococcus erythroprolis and an imine reductase from Streptosporangium roseum . Optimization of process parameters for cultivation and bioconversion led to substantial improvements in the initial laboratory procedure. The transformation of the methyl‐substituted diamine substrate to the N ‐heterocyclic product was successfully scaled‐up from shake‐flask to a 20 L bioreactor with increased substrate concentrations. Remarkably, we obtained 67 % of 3‐methylpiperidine product from 140 g substrate within 52 h.