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An improved process for biocatalytic asymmetric amine synthesis by in situ product removal using a supported liquid membrane

Rehn, Gustav LU ; Ayres, Bianca M LU ; Adlercreutz, Patrick LU and Grey, Carl LU (2016) In Journal of Molecular Catalysis B: Enzymatic 123. p.1-7
Abstract

Chiral amines are important building blocks in the pharmaceutical industry, and the biocatalytic synthesis of these compounds using ω-transaminases has been increasingly studied in recent years. In principal, asymmetric synthesis of chiral amines from a prochiral ketone is the preferable route, but it is often hampered by an unfavourable equilibrium position and product inhibition. An effective method for product removal is therefore necessary to drive the reaction towards product formation. In a recent study (Rehn et al., 2014) [29] we reported on the successful use of a supported liquid membrane (SLM) for the in situ product removal (ISPR) of (S)-α-methylbenzylamine (MBA) produced by Arthrobacter citreus ω-transaminase present in... (More)

Chiral amines are important building blocks in the pharmaceutical industry, and the biocatalytic synthesis of these compounds using ω-transaminases has been increasingly studied in recent years. In principal, asymmetric synthesis of chiral amines from a prochiral ketone is the preferable route, but it is often hampered by an unfavourable equilibrium position and product inhibition. An effective method for product removal is therefore necessary to drive the reaction towards product formation. In a recent study (Rehn et al., 2014) [29] we reported on the successful use of a supported liquid membrane (SLM) for the in situ product removal (ISPR) of (S)-α-methylbenzylamine (MBA) produced by Arthrobacter citreus ω-transaminase present in immobilized Escherichia coli cells. In the present work, we thoroughly discuss the factors influencing the performance of the SLM system and considerations for its successful use. Moreover, the system is further improved by implementing continuous control of the reactor pH using the amine donor substrate, and regeneration of the SLM unit at regular intervals to maintain the extraction performance, allowing the accumulation of 1.0 M (121 g/l) product in the stripping phase during operation for 91 h.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Chiral amines, In situ product removal (ISPR), Omega-transaminase, Supported liquid membrane
in
Journal of Molecular Catalysis B: Enzymatic
volume
123
pages
1 - 7
publisher
Elsevier
external identifiers
  • Scopus:84946606365
ISSN
1381-1177
DOI
10.1016/j.molcatb.2015.10.010
language
English
LU publication?
yes
id
59d7f273-1450-444d-a37d-696d253941c3
date added to LUP
2016-06-16 10:36:54
date last changed
2016-06-16 10:36:54
@misc{59d7f273-1450-444d-a37d-696d253941c3,
  abstract     = {<p>Chiral amines are important building blocks in the pharmaceutical industry, and the biocatalytic synthesis of these compounds using ω-transaminases has been increasingly studied in recent years. In principal, asymmetric synthesis of chiral amines from a prochiral ketone is the preferable route, but it is often hampered by an unfavourable equilibrium position and product inhibition. An effective method for product removal is therefore necessary to drive the reaction towards product formation. In a recent study (Rehn et al., 2014) [29] we reported on the successful use of a supported liquid membrane (SLM) for the in situ product removal (ISPR) of (S)-α-methylbenzylamine (MBA) produced by Arthrobacter citreus ω-transaminase present in immobilized Escherichia coli cells. In the present work, we thoroughly discuss the factors influencing the performance of the SLM system and considerations for its successful use. Moreover, the system is further improved by implementing continuous control of the reactor pH using the amine donor substrate, and regeneration of the SLM unit at regular intervals to maintain the extraction performance, allowing the accumulation of 1.0 M (121 g/l) product in the stripping phase during operation for 91 h.</p>},
  author       = {Rehn, Gustav and Ayres, Bianca M and Adlercreutz, Patrick and Grey, Carl},
  issn         = {1381-1177},
  keyword      = {Chiral amines,In situ product removal (ISPR),Omega-transaminase,Supported liquid membrane},
  language     = {eng},
  month        = {01},
  pages        = {1--7},
  publisher    = {ARRAY(0x9320928)},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {An improved process for biocatalytic asymmetric amine synthesis by in situ product removal using a supported liquid membrane},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2015.10.010},
  volume       = {123},
  year         = {2016},
}