Please use this identifier to cite or link to this item: https://doi.org/10.15480/882.2238
DC FieldValueLanguage
dc.contributor.authorBerheide, Marco-
dc.contributor.authorKara, Selin-
dc.contributor.authorLiese, Andreas-
dc.date.accessioned2019-05-07T14:00:08Z-
dc.date.available2019-05-07T14:00:08Z-
dc.date.issued2015-02-03-
dc.identifier.citationCatalysis Science & Technology (5): 2418-2426 (2015)de_DE
dc.identifier.issn2044-4761de_DE
dc.identifier.urihttp://hdl.handle.net/11420/2612-
dc.description.abstractBenzoylformate decarboxylase (BFD) from Pseudomonas putida catalyzed the formation of 2-hydroxy-1-phenylpropanone (2-HPP), a 2-hydroxy ketone, from the kinetic resolution of rac-benzoin in the presence of acetaldehyde. The formation rate of 2-HPP via kinetic resolution of benzoin was 700-fold lower compared to the formation via direct carboligation of benzaldehyde and acetaldehyde. Further investigations revealed that BFD not only accepts (R)-benzoin but also 2-HPP as the substrate. A typical Michaelis–Menten type kinetics was observed starting from enantiopure (S)- or (R)-2-HPP. The formation of racemic 2-HPP while using benzoin as the donor in the presence of acetaldehyde and the racemization of (R/S)-2-HPP were detected. The equilibrium constant determined, showed favoured conditions towards the product side i.e. (R)-benzoin and 2-HPP. In the end, an extended reaction mechanism was proposed by supplementing the already known mechanism with the C-C bond cleavage activity of BFD towards 2-hydroxy ketones.en
dc.language.isoende_DE
dc.publisherRoyal Society of Chemistry (RSC)de_DE
dc.relation.ispartofCatalysis science & technologyde_DE
dc.rightsCC BY 3.0de_DE
dc.rightsinfo:eu-repo/semantics/openAccess-
dc.subject.ddc500: Naturwissenschaftende_DE
dc.titleReversibility of asymmetric catalyzed C-C bond formation by benzoylformate decarboxylasede_DE
dc.typeArticlede_DE
dc.identifier.urnurn:nbn:de:gbv:830-882.034183-
dc.identifier.doi10.15480/882.2238-
dc.type.diniarticle-
dc.subject.ddccode500-
dcterms.DCMITypeText-
tuhh.identifier.urnurn:nbn:de:gbv:830-882.034183-
tuhh.oai.showtruede_DE
tuhh.abstract.englishBenzoylformate decarboxylase (BFD) from Pseudomonas putida catalyzed the formation of 2-hydroxy-1-phenylpropanone (2-HPP), a 2-hydroxy ketone, from the kinetic resolution of rac-benzoin in the presence of acetaldehyde. The formation rate of 2-HPP via kinetic resolution of benzoin was 700-fold lower compared to the formation via direct carboligation of benzaldehyde and acetaldehyde. Further investigations revealed that BFD not only accepts (R)-benzoin but also 2-HPP as the substrate. A typical Michaelis–Menten type kinetics was observed starting from enantiopure (S)- or (R)-2-HPP. The formation of racemic 2-HPP while using benzoin as the donor in the presence of acetaldehyde and the racemization of (R/S)-2-HPP were detected. The equilibrium constant determined, showed favoured conditions towards the product side i.e. (R)-benzoin and 2-HPP. In the end, an extended reaction mechanism was proposed by supplementing the already known mechanism with the C-C bond cleavage activity of BFD towards 2-hydroxy ketones.de_DE
tuhh.publisher.doi10.1039/C4CY00171K-
tuhh.publication.instituteTechnische Biokatalyse V-6de_DE
tuhh.identifier.doi10.15480/882.2238-
tuhh.type.opus(wissenschaftlicher) Artikel-
tuhh.institute.germanTechnische Biokatalyse V-6de
tuhh.institute.englishTechnische Biokatalyse V-6de_DE
tuhh.gvk.hasppnfalse-
openaire.rightsinfo:eu-repo/semantics/openAccessde_DE
dc.type.driverarticle-
dc.rights.cchttps://creativecommons.org/licenses/by/3.0/de_DE
dc.type.casraiJournal Article-
tuhh.container.volume5de_DE
tuhh.container.startpage2418de_DE
tuhh.container.endpage2426de_DE
dc.rights.nationallicensefalsede_DE
item.grantfulltextopen-
item.openairetypeArticle-
item.creatorGNDBerheide, Marco-
item.creatorGNDKara, Selin-
item.creatorGNDLiese, Andreas-
item.creatorOrcidBerheide, Marco-
item.creatorOrcidKara, Selin-
item.creatorOrcidLiese, Andreas-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_6501-
item.fulltextWith Fulltext-
item.cerifentitytypePublications-
crisitem.author.deptTechnische Biokatalyse V-6-
crisitem.author.deptTechnische Biokatalyse V-6-
crisitem.author.deptTechnische Biokatalyse V-6-
crisitem.author.orcid0000-0001-6754-2814-
crisitem.author.orcid0000-0002-4867-9935-
crisitem.author.parentorgStudiendekanat Verfahrenstechnik-
crisitem.author.parentorgStudiendekanat Verfahrenstechnik-
crisitem.author.parentorgStudiendekanat Verfahrenstechnik-
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