Advanced

A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

Börner, Tim LU ; Rehn, Gustav; Grey, Carl LU and Adlercreutz, Patrick LU (2015) In Organic Process Research & Development 19(7). p.793-799
Abstract
For the amine transaminase (ATA)-catalyzed synthesis of chiral amines, the choice of donor substrate is of high importance for reaction and process design. Alanine was investigated as an amine donor for the reductive amination of a poorly water-soluble ketone (4-phenyl-2-butanone) in a combined in situ product removal (ISPR) approach using liquid-membrane extraction together with an enzyme cascade. This ISPR strategy facilitates very high (>98%) product purity with an integrated enrichment step and eliminates product as well as coproduct inhibition. In the presented proof-of-concept alanine shows the following advantages over the other frequently employed amine donor isopropyl amine: (i) nonextractability of alanine affords high product... (More)
For the amine transaminase (ATA)-catalyzed synthesis of chiral amines, the choice of donor substrate is of high importance for reaction and process design. Alanine was investigated as an amine donor for the reductive amination of a poorly water-soluble ketone (4-phenyl-2-butanone) in a combined in situ product removal (ISPR) approach using liquid-membrane extraction together with an enzyme cascade. This ISPR strategy facilitates very high (>98%) product purity with an integrated enrichment step and eliminates product as well as coproduct inhibition. In the presented proof-of-concept alanine shows the following advantages over the other frequently employed amine donor isopropyl amine: (i) nonextractability of alanine affords high product purity without any additional downstream step and no losses via coextraction, (ii) higher maximum reaction rates, and (iii) broader acceptance among ATAs. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Process Research & Development
volume
19
issue
7
pages
793 - 799
publisher
The American Chemical Society
external identifiers
  • wos:000358395000012
  • scopus:84937153016
ISSN
1083-6160
DOI
10.1021/acs.oprd.5b00055
language
English
LU publication?
yes
id
6433379a-4207-45fb-b91d-554e54cc9f7a (old id 7773496)
date added to LUP
2015-09-18 15:33:52
date last changed
2017-10-29 03:01:36
@article{6433379a-4207-45fb-b91d-554e54cc9f7a,
  abstract     = {For the amine transaminase (ATA)-catalyzed synthesis of chiral amines, the choice of donor substrate is of high importance for reaction and process design. Alanine was investigated as an amine donor for the reductive amination of a poorly water-soluble ketone (4-phenyl-2-butanone) in a combined in situ product removal (ISPR) approach using liquid-membrane extraction together with an enzyme cascade. This ISPR strategy facilitates very high (>98%) product purity with an integrated enrichment step and eliminates product as well as coproduct inhibition. In the presented proof-of-concept alanine shows the following advantages over the other frequently employed amine donor isopropyl amine: (i) nonextractability of alanine affords high product purity without any additional downstream step and no losses via coextraction, (ii) higher maximum reaction rates, and (iii) broader acceptance among ATAs.},
  author       = {Börner, Tim and Rehn, Gustav and Grey, Carl and Adlercreutz, Patrick},
  issn         = {1083-6160},
  language     = {eng},
  number       = {7},
  pages        = {793--799},
  publisher    = {The American Chemical Society},
  series       = {Organic Process Research & Development},
  title        = {A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR},
  url          = {http://dx.doi.org/10.1021/acs.oprd.5b00055},
  volume       = {19},
  year         = {2015},
}