Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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 amination of alcohols by combining oxidation catalysts with transaminases in one pot
KTH, School of Biotechnology (BIO), Industrial Biotechnology.
KTH, School of Biotechnology (BIO), Industrial Biotechnology.ORCID iD: 0000-0002-9577-832X
(English)Manuscript (preprint) (Other academic)
Abstract [en]

Chemoenzymatic methods for the amination of alcohols have been developed. The reactions were performed in a one-pot two-step fashion, where the alcohol starting material was first oxidized to the corresponding carbonyl compound and then subsequently converted to the amine product with an enzymatic system based on an amine transaminase. The enzyme system was able to operate in a water/organic solvent two-phase system in the presence of either a heterogeneous palladium(0) catalyst or a homogeneous copper(I) catalyst. High conversions to the product amines were achieved for a range of substituted benzyl alcohols and similar compounds, but unfortunately the use of aliphatic alcohols resulted in lower conversions and secondary alcohols could not be converted to the corresponding amines with this methodology.

Keywords [en]
Biocatalysis, enzyme, amine transaminase, ω-transaminase, green chemistry, palladium, copper, TEMPO
National Category
Organic Chemistry
Research subject
Biotechnology
Identifiers
URN: urn:nbn:se:kth:diva-199644OAI: oai:DiVA.org:kth-199644DiVA, id: diva2:1064491
Note

QC 20170117

Available from: 2017-01-12 Created: 2017-01-12 Last updated: 2017-01-23Bibliographically approved
In thesis
1. Amine Transaminases in Multi-Step One-Pot Reactions
Open this publication in new window or tab >>Amine Transaminases in Multi-Step One-Pot Reactions
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Amine transaminases are enzymes that catalyze the mild and selective formation of primary amines, which are useful building blocks for biologically active compounds and natural products. In order to make the production of these kinds of compounds more efficient from both a practical and an environmental point of view, amine transaminases were incorporated into multi-step one-pot reactions. With this kind of methodology there is no need for isolation of intermediates, and thus unnecessary work-up steps can be omitted and formation of waste is prevented. Amine transaminases were successfully combined with other enzymes for multi-step synthesis of valuable products: With ketoreductases all four diastereomers of a 1,3-amino alcohol could be obtained, and the use of a lipase allowed for the synthesis of natural products in the form of capsaicinoids. Amine transaminases were also successfully combined with metal catalysts based on palladium or copper. This methodology allowed for the amination of alcohols and the synthesis of chiral amines such as the pharmaceutical compound Rivastigmine. These examples show that the use of amine transaminases in multi-step one-pot reactions is possible, and hopefully this concept can be further developed and applied to make industrial processes more sustainable and efficient in the future.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2017. p. 58
Series
TRITA-BIO-Report, ISSN 1654-2312 ; 2017:3
Keywords
Biocatalysis, enzyme, amine transaminase, ω-transaminase, amination, primary amine, chiral amine, chemoenzymatic, green chemistry, synthesis, cascade
National Category
Biochemistry and Molecular Biology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-199646 (URN)978-91-7729-254-8 (ISBN)
Public defence
2017-02-17, Kollegiesalen, Brinellvägen 8, KTH, 10:00 (English)
Opponent
Supervisors
Note

QC 20170113

Available from: 2017-01-13 Created: 2017-01-12 Last updated: 2017-01-13Bibliographically approved

Open Access in DiVA

No full text in DiVA

Authority records BETA

Berglund, Per

Search in DiVA

By author/editor
Anderson, MattiasBerglund, Per
By organisation
Industrial Biotechnology
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric score

urn-nbn
Total: 910 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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