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:
https://lup.lub.lu.se/record/7773496
- author
- Börner, Tim
LU
; Rehn, Gustav
; Grey, Carl
LU
and Adlercreutz, Patrick
LU
- organization
- publishing date
- 2015
- 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 (ACS)
- 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
- 2016-04-01 09:53:15
- date last changed
- 2022-02-17 04:32:25
@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 (ACS)}},
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}},
doi = {{10.1021/acs.oprd.5b00055}},
volume = {{19}},
year = {{2015}},
}