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Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot
AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5108-6487
AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
2014 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 9, 2113-2118 p.Article in journal (Refereed) 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.

Place, publisher, year, edition, pages
2014. Vol. 356, no 9, 2113-2118 p.
Keyword [en]
aldol reaction, amine transferase, biocatalysis, capsaicin analogues, oxidation, palladium, renewable resources
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-22585DOI: 10.1002/adsc.201301148ISI: 000337609400023Scopus ID: 2-s2.0-84902535619OAI: oai:DiVA.org:miun-22585DiVA: diva2:739195
Available from: 2014-08-20 Created: 2014-08-19 Last updated: 2016-09-29Bibliographically approved

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