Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Chemoenzymatic Synthesis of Sertraline
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Industrial Biotechnology.
Show others and affiliations
2020 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2020, no 4, p. 510-513Article in journal (Refereed) Published
Abstract [en]

A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2020. Vol. 2020, no 4, p. 510-513
Keywords [en]
Asymmetric catalysis, Biocatalysis, Ketoreductases, Medicinal chemistry, Synthetic methods
National Category
Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
URN: urn:nbn:se:kth:diva-266975DOI: 10.1002/ejoc.201901810ISI: 000507589300001Scopus ID: 2-s2.0-85078385263OAI: oai:DiVA.org:kth-266975DiVA, id: diva2:1389100
Funder
EU, Horizon 2020, 634200
Note

QC 20200129

Available from: 2020-01-28 Created: 2020-01-28 Last updated: 2020-02-04Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textScopushttps://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201901810

Authority records BETA

Marx, LisaBerglund, Per

Search in DiVA

By author/editor
Marx, LisaBerglund, Per
By organisation
Industrial Biotechnology
In the same journal
European Journal of Organic Chemistry
Biocatalysis and Enzyme Technology

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 12 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf