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Chemoenzymatic amination of alcohols by combining oxidation catalysts with transaminases in one pot
KTH, Skolan för bioteknologi (BIO), Industriell bioteknologi.
KTH, Skolan för bioteknologi (BIO), Industriell bioteknologi.ORCID-id: 0000-0002-9577-832X
(engelsk)Manuskript (preprint) (Annet vitenskapelig)
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.

Emneord [en]
Biocatalysis, enzyme, amine transaminase, ω-transaminase, green chemistry, palladium, copper, TEMPO
HSV kategori
Forskningsprogram
Bioteknologi
Identifikatorer
URN: urn:nbn:se:kth:diva-199644OAI: oai:DiVA.org:kth-199644DiVA, id: diva2:1064491
Merknad

QC 20170117

Tilgjengelig fra: 2017-01-12 Laget: 2017-01-12 Sist oppdatert: 2017-01-23bibliografisk kontrollert
Inngår i avhandling
1. Amine Transaminases in Multi-Step One-Pot Reactions
Åpne denne publikasjonen i ny fane eller vindu >>Amine Transaminases in Multi-Step One-Pot Reactions
2017 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2017. s. 58
Serie
TRITA-BIO-Report, ISSN 1654-2312 ; 2017:3
Emneord
Biocatalysis, enzyme, amine transaminase, ω-transaminase, amination, primary amine, chiral amine, chemoenzymatic, green chemistry, synthesis, cascade
HSV kategori
Forskningsprogram
Bioteknologi
Identifikatorer
urn:nbn:se:kth:diva-199646 (URN)978-91-7729-254-8 (ISBN)
Disputas
2017-02-17, Kollegiesalen, Brinellvägen 8, KTH, 10:00 (engelsk)
Opponent
Veileder
Merknad

QC 20170113

Tilgjengelig fra: 2017-01-13 Laget: 2017-01-12 Sist oppdatert: 2017-01-13bibliografisk kontrollert

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