Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot

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Fältnamn	Indikatorer	Metadata
000		03929naa a2200529 4500
001		oai:DiVA.org:kth-148291
003		SwePub
008		140805s2014 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
009		oai:DiVA.org:miun-22585
009		oai:DiVA.org:su-106068
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-1482912 URI
024	7	a https://doi.org/10.1002/adsc.2013011482 DOI
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:miun:diva-225852 URI
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-1060682 URI
040		a (SwePub)kthd (SwePub)miund (SwePub)su
041		a engb eng
042		9 SwePub
072	7	a ref2 swepub-contenttype
072	7	a art2 swepub-publicationtype
100	1	a Anderson, Mattiasu KTH,Industriell bioteknologi,AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden4 aut0 (Swepub:kth)u1eqa8pn
245	1 0	a Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot
264		c 2014-04-15
264	1	b Wiley,c 2014
338		a print2 rdacarrier
500		a QC 20140807
500		a AuthorCount:4;
520		a 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.
650	7	a TEKNIK OCH TEKNOLOGIERx Industriell bioteknikx Bioprocessteknik0 (SwePub)209012 hsv//swe
650	7	a ENGINEERING AND TECHNOLOGYx Industrial Biotechnologyx Bioprocess Technology0 (SwePub)209012 hsv//eng
650	7	a NATURVETENSKAPx Kemix Organisk kemi0 (SwePub)104052 hsv//swe
650	7	a NATURAL SCIENCESx Chemical Sciencesx Organic Chemistry0 (SwePub)104052 hsv//eng
653		a aldol reaction
653		a amine transferase
653		a biocatalysis
653		a capsaicin analogues
653		a oxidation
653		a palladium
653		a renewable resources
700	1	a Afewerki, Samsonu Mittuniversitetet,Avdelningen för naturvetenskap4 aut0 (Swepub:miun)samafe
700	1	a Berglund, Peru KTH,Industriell bioteknologi,AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden4 aut0 (Swepub:kth)u1271chh
700	1	a Cordova, Armandou Stockholms universitet,Mittuniversitetet,Avdelningen för naturvetenskap,Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden,Institutionen för organisk kemi,Mid Sweden University, Sweden4 aut0 (Swepub:su)acr
710	2	a KTHb Industriell bioteknologi4 org
773	0	t Advanced Synthesis and Catalysisd : Wileyg 356:9, s. 2113-2118q 356:9<2113-2118x 1615-4150x 1615-4169
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-148291
856	4 8	u https://doi.org/10.1002/adsc.201301148
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:miun:diva-22585
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-106068

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