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Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot
KTH, Skolan för bioteknologi (BIO), Industriell bioteknologi.
KTH, Skolan för bioteknologi (BIO), Industriell bioteknologi.ORCID-id: 0000-0002-9577-832X
2014 (engelsk)Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, nr 9, s. 2113-2118Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillyl-amine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using l-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

sted, utgiver, år, opplag, sider
2014. Vol. 356, nr 9, s. 2113-2118
Emneord [en]
aldol reaction, amine transferase, biocatalysis, capsaicin analogues, oxidation, palladium, renewable resources
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-148291DOI: 10.1002/adsc.201301148ISI: 000337609400023Scopus ID: 2-s2.0-84902535619OAI: oai:DiVA.org:kth-148291DiVA, id: diva2:736598
Forskningsfinansiär
Swedish Research CouncilVinnova
Merknad

QC 20140807

Tilgjengelig fra: 2014-08-07 Laget: 2014-08-05 Sist oppdatert: 2017-12-05bibliografisk 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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