TUHH Open Research
Help
  • Log In
    New user? Click here to register.Have you forgotten your password?
  • English
  • Deutsch
  • Communities & Collections
  • Publications
  • Research Data
  • People
  • Institutions
  • Projects
  • Statistics
  1. Home
  2. TUHH
  3. Publication References
  4. Development of a continuously operating process for the enantioselective synthesis of a b-amino acid ester via a solvent-free chemoenzymatic reaction sequence
 
Options

Development of a continuously operating process for the enantioselective synthesis of a b-amino acid ester via a solvent-free chemoenzymatic reaction sequence

Publikationstyp
Journal Article
Date Issued
2013-08-09
Sprache
English
Author(s)
Strompen, Simon  
Weiß, Markus  
Gröger, Harald  
Hilterhaus, Lutz  
Liese, Andreas  orcid-logo
Institut
Technische Biokatalyse V-6  
TORE-URI
http://hdl.handle.net/11420/6579
Journal
Advanced synthesis & catalysis  
Volume
355
Issue
11-12
Start Page
2391
End Page
2399
Citation
Advanced Synthesis and Catalysis 11-12 (355): 2391-2399 (2013)
Publisher DOI
10.1002/adsc.201300236
Scopus ID
2-s2.0-84884500315
Publisher
Wiley-VCH
A sequential, chemoenzymatic process for a continuously operating production of the chiral β-amino acid ester ethyl (S)-3-(benzylamino)- butanoate was developed. The reactor set-up combined a plug-flow reactor for the thermal aza-Michael addition of benzylamine to trans-ethyl crotonate coupled to a subsequent packed-bed reactor for the lipase (Novozym 435)-catalyzed kinetic resolution of the racemic intermediate product, which was formed in the initial step. The coupled reactors were operated continuously for a time period of 4 days without significant loss of enzyme activity. The target β-amino acid ester was obtained with 92% conversion in the plug-flow reactor and 59% conversion in the packed bed reactor at high enantiomeric excess of >98%. A space-time yield of 0.4 kgL-1d-1 was calculated for the total reactor system and 1.8 kgL-1d-1 based solely on the volume of the packed bed reactor. A total turnover number of 158,000 was calculated for the biocatalyst assuming the same deactivation rate as observed in batch experiments. The continuously operating, solvent-free process thus represents an efficient method for the enantioselective production of a value added (S)-β-amino acid ester starting from cheap substrates. © 2013 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
Subjects
β-amino acids
Biocatalysis
Chemoenzymatic reaction sequence
Continuously operating process
Kinetic resolution
Solvent-free conditions
DDC Class
570: Biowissenschaften, Biologie
TUHH
Weiterführende Links
  • Contact
  • Send Feedback
  • Cookie settings
  • Privacy policy
  • Impress
DSpace Software

Built with DSpace-CRIS software - Extension maintained and optimized by 4Science
Design by effective webwork GmbH

  • Deutsche NationalbibliothekDeutsche Nationalbibliothek
  • ORCiD Member OrganizationORCiD Member Organization
  • DataCiteDataCite
  • Re3DataRe3Data
  • OpenDOAROpenDOAR
  • OpenAireOpenAire
  • BASE Bielefeld Academic Search EngineBASE Bielefeld Academic Search Engine
Feedback