An ADH toolbox for raspberry ketone production from natural resources via a biocatalytic cascade
Raspberry ketone is a widely used flavor compound in food and cosmetic industry. Several processes for its biocatalytic production have already been described, but either with the use of genetically modified organisms (GMOs) or incomplete conversion of the variety of precursors that are available in...
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| Veröffentlicht in: | Applied microbiology and biotechnology 2021-05, Vol.105 (10), p.4189-4197 |
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| creator | Becker, Aileen Böttcher, Dominique Katzer, Werner Siems, Karsten Müller-Kuhrt, Lutz Bornscheuer, Uwe T. |
| description | Raspberry ketone is a widely used flavor compound in food and cosmetic industry. Several processes for its biocatalytic production have already been described, but either with the use of genetically modified organisms (GMOs) or incomplete conversion of the variety of precursors that are available in nature. Such natural precursors are rhododendrol glycosides with different proportions of (
R
)- and (
S
)-rhododendrol depending on the origin. After hydrolysis of these rhododendrol glycosides, the formed rhododendrol enantiomers have to be oxidized to obtain the final product raspberry ketone. To be able to achieve a high conversion with different starting material, we assembled an alcohol dehydrogenase toolbox that can be accessed depending on the optical purity of the intermediate rhododendrol. This is demonstrated by converting racemic rhododendrol using a combination of (
R
)- and (
S
)-selective alcohol dehydrogenases together with a universal cofactor recycling system. Furthermore, we conducted a biocatalytic cascade reaction starting from naturally derived rhododendrol glycosides by the use of a glucosidase and an alcohol dehydrogenase to produce raspberry ketone in high yield.
Key points
•
LB-ADH, LK-ADH and LS-ADH oxidize (R)-rhododendrol
•
RR-ADH and ADH1E oxidize (S)-rhododendrol
•
Raspberry ketone production via glucosidase and alcohol dehydrogenases from a toolbox
Graphical abstract |
| doi_str_mv | 10.1007/s00253-021-11332-9 |
| format | Article |
| fullrecord | <record><control><sourceid>gale_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8140976</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A662708599</galeid><sourcerecordid>A662708599</sourcerecordid><originalsourceid>FETCH-LOGICAL-c612t-f6a7b5aa1603f0c8e27bc3ae369c257cf82b1b8b6ee3360d1512344d8d64f4ed3</originalsourceid><addsrcrecordid>eNp9kktv1DAUhSMEokPhD7BAltjAIsWP-JEN0qg8WqkSEo-1cZzrwSWJB9upOv8ehyktgxArW77fObaPTlU9JfiEYCxfJYwpZzWmpCaEMVq396oVacoGC9Lcr1aYSF5L3qqj6lFKlxgTqoR4WB0x1iolGV9VX9cTWr85QzmEoQvXyIWIoknbDmLcoe-QwwRoG0M_2-zDhFwMI5pMnqMZUIQU5mghoStvkEGdD9ZkM-yyt8iaZE0Pj6sHzgwJntysx9WXd28_n57VFx_en5-uL2orCM21E0Z23BgiMHPYKqCys8wAE62lXFqnaEc61QkAxgTuCSeUNU2vetG4Bnp2XL3e-27nboTewpTLE_U2-tHEnQ7G68PJ5L_pTbjSijS4laIYvLgxiOHHDCnr0ScLw2AmCHPSlFNFZCvogj7_C70sOUzle4VimC928o7amAG0n1wo99rFVK-FoBIr3raFOvkHZZboRm9L-s6X8wPBywNBYTJc542ZU9Lnnz4esnTP2hhSiuBu8yBYLx3S-w7p0iH9q0N6ET37M8lbye_SFIDtgVRG0wbi3ff_Y_sTuZPQ8w</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2530597637</pqid></control><display><type>article</type><title>An ADH toolbox for raspberry ketone production from natural resources via a biocatalytic cascade</title><source>SpringerLink Journals - AutoHoldings</source><creator>Becker, Aileen ; Böttcher, Dominique ; Katzer, Werner ; Siems, Karsten ; Müller-Kuhrt, Lutz ; Bornscheuer, Uwe T.</creator><creatorcontrib>Becker, Aileen ; Böttcher, Dominique ; Katzer, Werner ; Siems, Karsten ; Müller-Kuhrt, Lutz ; Bornscheuer, Uwe T.</creatorcontrib><description>Raspberry ketone is a widely used flavor compound in food and cosmetic industry. Several processes for its biocatalytic production have already been described, but either with the use of genetically modified organisms (GMOs) or incomplete conversion of the variety of precursors that are available in nature. Such natural precursors are rhododendrol glycosides with different proportions of (
R
)- and (
S
)-rhododendrol depending on the origin. After hydrolysis of these rhododendrol glycosides, the formed rhododendrol enantiomers have to be oxidized to obtain the final product raspberry ketone. To be able to achieve a high conversion with different starting material, we assembled an alcohol dehydrogenase toolbox that can be accessed depending on the optical purity of the intermediate rhododendrol. This is demonstrated by converting racemic rhododendrol using a combination of (
R
)- and (
S
)-selective alcohol dehydrogenases together with a universal cofactor recycling system. Furthermore, we conducted a biocatalytic cascade reaction starting from naturally derived rhododendrol glycosides by the use of a glucosidase and an alcohol dehydrogenase to produce raspberry ketone in high yield.
Key points
•
LB-ADH, LK-ADH and LS-ADH oxidize (R)-rhododendrol
•
RR-ADH and ADH1E oxidize (S)-rhododendrol
•
Raspberry ketone production via glucosidase and alcohol dehydrogenases from a toolbox
Graphical abstract</description><identifier>ISSN: 0175-7598</identifier><identifier>EISSN: 1432-0614</identifier><identifier>DOI: 10.1007/s00253-021-11332-9</identifier><identifier>PMID: 33988735</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Alcohol ; Alcohol dehydrogenase ; Alcohols ; Aroma compounds ; Biomedical and Life Sciences ; Biosynthesis ; Biotechnologically Relevant Enzymes and Proteins ; Biotechnology ; Cascade chemical reactions ; Conversion ; Dehydrogenase ; Dehydrogenases ; Enantiomers ; Flavor compounds ; Food industry ; Fruits ; Genetic modification ; Genetically engineered organisms ; Genetically modified organisms ; Glucosidase ; Glycosides ; Ketones ; Life Sciences ; Methods ; Microbial Genetics and Genomics ; Microbiology ; Natural resources ; Physiological aspects ; Precursors ; Raspberries ; Recycling systems</subject><ispartof>Applied microbiology and biotechnology, 2021-05, Vol.105 (10), p.4189-4197</ispartof><rights>The Author(s) 2021</rights><rights>COPYRIGHT 2021 Springer</rights><rights>The Author(s) 2021. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c612t-f6a7b5aa1603f0c8e27bc3ae369c257cf82b1b8b6ee3360d1512344d8d64f4ed3</citedby><cites>FETCH-LOGICAL-c612t-f6a7b5aa1603f0c8e27bc3ae369c257cf82b1b8b6ee3360d1512344d8d64f4ed3</cites><orcidid>0000-0003-0685-2696</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00253-021-11332-9$$EPDF$$P50$$Gspringer$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00253-021-11332-9$$EHTML$$P50$$Gspringer$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33988735$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Becker, Aileen</creatorcontrib><creatorcontrib>Böttcher, Dominique</creatorcontrib><creatorcontrib>Katzer, Werner</creatorcontrib><creatorcontrib>Siems, Karsten</creatorcontrib><creatorcontrib>Müller-Kuhrt, Lutz</creatorcontrib><creatorcontrib>Bornscheuer, Uwe T.</creatorcontrib><title>An ADH toolbox for raspberry ketone production from natural resources via a biocatalytic cascade</title><title>Applied microbiology and biotechnology</title><addtitle>Appl Microbiol Biotechnol</addtitle><addtitle>Appl Microbiol Biotechnol</addtitle><description>Raspberry ketone is a widely used flavor compound in food and cosmetic industry. Several processes for its biocatalytic production have already been described, but either with the use of genetically modified organisms (GMOs) or incomplete conversion of the variety of precursors that are available in nature. Such natural precursors are rhododendrol glycosides with different proportions of (
R
)- and (
S
)-rhododendrol depending on the origin. After hydrolysis of these rhododendrol glycosides, the formed rhododendrol enantiomers have to be oxidized to obtain the final product raspberry ketone. To be able to achieve a high conversion with different starting material, we assembled an alcohol dehydrogenase toolbox that can be accessed depending on the optical purity of the intermediate rhododendrol. This is demonstrated by converting racemic rhododendrol using a combination of (
R
)- and (
S
)-selective alcohol dehydrogenases together with a universal cofactor recycling system. Furthermore, we conducted a biocatalytic cascade reaction starting from naturally derived rhododendrol glycosides by the use of a glucosidase and an alcohol dehydrogenase to produce raspberry ketone in high yield.
Key points
•
LB-ADH, LK-ADH and LS-ADH oxidize (R)-rhododendrol
•
RR-ADH and ADH1E oxidize (S)-rhododendrol
•
Raspberry ketone production via glucosidase and alcohol dehydrogenases from a toolbox
Graphical abstract</description><subject>Alcohol</subject><subject>Alcohol dehydrogenase</subject><subject>Alcohols</subject><subject>Aroma compounds</subject><subject>Biomedical and Life Sciences</subject><subject>Biosynthesis</subject><subject>Biotechnologically Relevant Enzymes and Proteins</subject><subject>Biotechnology</subject><subject>Cascade chemical reactions</subject><subject>Conversion</subject><subject>Dehydrogenase</subject><subject>Dehydrogenases</subject><subject>Enantiomers</subject><subject>Flavor compounds</subject><subject>Food industry</subject><subject>Fruits</subject><subject>Genetic modification</subject><subject>Genetically engineered organisms</subject><subject>Genetically modified organisms</subject><subject>Glucosidase</subject><subject>Glycosides</subject><subject>Ketones</subject><subject>Life Sciences</subject><subject>Methods</subject><subject>Microbial Genetics and Genomics</subject><subject>Microbiology</subject><subject>Natural resources</subject><subject>Physiological aspects</subject><subject>Precursors</subject><subject>Raspberries</subject><subject>Recycling 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ADH toolbox for raspberry ketone production from natural resources via a biocatalytic cascade</title><author>Becker, Aileen ; Böttcher, Dominique ; Katzer, Werner ; Siems, Karsten ; Müller-Kuhrt, Lutz ; Bornscheuer, Uwe T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c612t-f6a7b5aa1603f0c8e27bc3ae369c257cf82b1b8b6ee3360d1512344d8d64f4ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alcohol</topic><topic>Alcohol dehydrogenase</topic><topic>Alcohols</topic><topic>Aroma compounds</topic><topic>Biomedical and Life Sciences</topic><topic>Biosynthesis</topic><topic>Biotechnologically Relevant Enzymes and Proteins</topic><topic>Biotechnology</topic><topic>Cascade chemical reactions</topic><topic>Conversion</topic><topic>Dehydrogenase</topic><topic>Dehydrogenases</topic><topic>Enantiomers</topic><topic>Flavor compounds</topic><topic>Food industry</topic><topic>Fruits</topic><topic>Genetic modification</topic><topic>Genetically engineered organisms</topic><topic>Genetically modified organisms</topic><topic>Glucosidase</topic><topic>Glycosides</topic><topic>Ketones</topic><topic>Life Sciences</topic><topic>Methods</topic><topic>Microbial Genetics and Genomics</topic><topic>Microbiology</topic><topic>Natural resources</topic><topic>Physiological aspects</topic><topic>Precursors</topic><topic>Raspberries</topic><topic>Recycling systems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Becker, Aileen</creatorcontrib><creatorcontrib>Böttcher, Dominique</creatorcontrib><creatorcontrib>Katzer, Werner</creatorcontrib><creatorcontrib>Siems, Karsten</creatorcontrib><creatorcontrib>Müller-Kuhrt, Lutz</creatorcontrib><creatorcontrib>Bornscheuer, Uwe T.</creatorcontrib><collection>Springer Nature OA/Free 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biotechnology</jtitle><stitle>Appl Microbiol Biotechnol</stitle><addtitle>Appl Microbiol Biotechnol</addtitle><date>2021-05-01</date><risdate>2021</risdate><volume>105</volume><issue>10</issue><spage>4189</spage><epage>4197</epage><pages>4189-4197</pages><issn>0175-7598</issn><eissn>1432-0614</eissn><abstract>Raspberry ketone is a widely used flavor compound in food and cosmetic industry. Several processes for its biocatalytic production have already been described, but either with the use of genetically modified organisms (GMOs) or incomplete conversion of the variety of precursors that are available in nature. Such natural precursors are rhododendrol glycosides with different proportions of (
R
)- and (
S
)-rhododendrol depending on the origin. After hydrolysis of these rhododendrol glycosides, the formed rhododendrol enantiomers have to be oxidized to obtain the final product raspberry ketone. To be able to achieve a high conversion with different starting material, we assembled an alcohol dehydrogenase toolbox that can be accessed depending on the optical purity of the intermediate rhododendrol. This is demonstrated by converting racemic rhododendrol using a combination of (
R
)- and (
S
)-selective alcohol dehydrogenases together with a universal cofactor recycling system. Furthermore, we conducted a biocatalytic cascade reaction starting from naturally derived rhododendrol glycosides by the use of a glucosidase and an alcohol dehydrogenase to produce raspberry ketone in high yield.
Key points
•
LB-ADH, LK-ADH and LS-ADH oxidize (R)-rhododendrol
•
RR-ADH and ADH1E oxidize (S)-rhododendrol
•
Raspberry ketone production via glucosidase and alcohol dehydrogenases from a toolbox
Graphical abstract</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>33988735</pmid><doi>10.1007/s00253-021-11332-9</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-0685-2696</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0175-7598 |
| ispartof | Applied microbiology and biotechnology, 2021-05, Vol.105 (10), p.4189-4197 |
| issn | 0175-7598 1432-0614 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8140976 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Alcohol Alcohol dehydrogenase Alcohols Aroma compounds Biomedical and Life Sciences Biosynthesis Biotechnologically Relevant Enzymes and Proteins Biotechnology Cascade chemical reactions Conversion Dehydrogenase Dehydrogenases Enantiomers Flavor compounds Food industry Fruits Genetic modification Genetically engineered organisms Genetically modified organisms Glucosidase Glycosides Ketones Life Sciences Methods Microbial Genetics and Genomics Microbiology Natural resources Physiological aspects Precursors Raspberries Recycling systems |
| title | An ADH toolbox for raspberry ketone production from natural resources via a biocatalytic cascade |
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