Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]‐Hydrogenase
[Fe]‐hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]‐hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]‐hydrogenase....
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| Veröffentlicht in: | Angewandte Chemie 2020-03, Vol.132 (12), p.4972-4976 |
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| container_title | Angewandte Chemie |
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| creator | Pan, Hui‐Jie Hu, Xile |
| description | [Fe]‐hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]‐hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]‐hydrogenase. This complex exhibits the highest activity and broadest scope in catalytic hydrogenation among known mimics. Thanks to its biomimetic nature, the complex exhibits unique activity in the hydrogenation of compounds analogous to methenyl‐H4MPT+, the natural substrate of [Fe]‐hydrogenase. This activity enables asymmetric relay hydrogenation of benzoxazinones and benzoxazines, involving the hydrogenation of a chiral hydride transfer agent using our catalyst coupled to Lewis acid‐catalyzed hydride transfer from this agent to the substrates.
Ein Mangan(I)‐Komplex, der nach dem Vorbild der [Fe]‐Hydrogenase entwickelt wurde, weist unter den bekannten biomimetischen Verbindungendie höchste Aktivität und den größten Reaktionsumfang für katalytische Hydrierungen auf. Durch seinen biomimetischen Charakter zeigt er insbesondere eine einzigartige Aktivität in der Hydrierung von analogen Verbindungen zu Methenyl‐H4MPT+, dem natürlichen Substrat der [Fe]‐Hydrogenase. |
| doi_str_mv | 10.1002/ange.201914377 |
| format | Article |
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Ein Mangan(I)‐Komplex, der nach dem Vorbild der [Fe]‐Hydrogenase entwickelt wurde, weist unter den bekannten biomimetischen Verbindungendie höchste Aktivität und den größten Reaktionsumfang für katalytische Hydrierungen auf. Durch seinen biomimetischen Charakter zeigt er insbesondere eine einzigartige Aktivität in der Hydrierung von analogen Verbindungen zu Methenyl‐H4MPT+, dem natürlichen Substrat der [Fe]‐Hydrogenase.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201914377</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>[Fe]-Hydrogenase ; Benzoxazines ; Bioanorganische Chemie ; Biomimetic materials ; Biomimetics ; Biomimetische Chemie ; Catalysts ; Chemistry ; Coupling ; Hydrides ; Hydrierung ; Hydrogenase ; Hydrogenation ; Iron ; Lewis acid ; Mangan ; Manganese ; Mimicry ; Substrates</subject><ispartof>Angewandte Chemie, 2020-03, Vol.132 (12), p.4972-4976</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2027-ad5c3f0b4985677bb3c72f73446c1d451cdddda0ae6c720788906ce4f4f7007f3</citedby><cites>FETCH-LOGICAL-c2027-ad5c3f0b4985677bb3c72f73446c1d451cdddda0ae6c720788906ce4f4f7007f3</cites><orcidid>0000-0001-8335-1196</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201914377$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201914377$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Pan, Hui‐Jie</creatorcontrib><creatorcontrib>Hu, Xile</creatorcontrib><title>Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]‐Hydrogenase</title><title>Angewandte Chemie</title><description>[Fe]‐hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]‐hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]‐hydrogenase. This complex exhibits the highest activity and broadest scope in catalytic hydrogenation among known mimics. Thanks to its biomimetic nature, the complex exhibits unique activity in the hydrogenation of compounds analogous to methenyl‐H4MPT+, the natural substrate of [Fe]‐hydrogenase. This activity enables asymmetric relay hydrogenation of benzoxazinones and benzoxazines, involving the hydrogenation of a chiral hydride transfer agent using our catalyst coupled to Lewis acid‐catalyzed hydride transfer from this agent to the substrates.
Ein Mangan(I)‐Komplex, der nach dem Vorbild der [Fe]‐Hydrogenase entwickelt wurde, weist unter den bekannten biomimetischen Verbindungendie höchste Aktivität und den größten Reaktionsumfang für katalytische Hydrierungen auf. Durch seinen biomimetischen Charakter zeigt er insbesondere eine einzigartige Aktivität in der Hydrierung von analogen Verbindungen zu Methenyl‐H4MPT+, dem natürlichen Substrat der [Fe]‐Hydrogenase.</description><subject>[Fe]-Hydrogenase</subject><subject>Benzoxazines</subject><subject>Bioanorganische Chemie</subject><subject>Biomimetic materials</subject><subject>Biomimetics</subject><subject>Biomimetische Chemie</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>Hydrides</subject><subject>Hydrierung</subject><subject>Hydrogenase</subject><subject>Hydrogenation</subject><subject>Iron</subject><subject>Lewis acid</subject><subject>Mangan</subject><subject>Manganese</subject><subject>Mimicry</subject><subject>Substrates</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMltiTjk7Ti4ZS9UPpBYWmBCyHMeuUqVxiVOhMPET-I38ElIFlZFbbrjneU96CblmMGIA_FZVazPiwFImQsQTMmARZ0GIEZ6SAYAQQcJFek4uvN8AQMwxHZDVXeG2xdY0haaLNq_d2lSqKVxFJ6pRZfthcpq1VNFVF68q4w1dudyU1Fn6MjOv359fR82bS3JmVenN1e8ekufZ9GmyCJaP8_vJeBloDhwDlUc6tJCJNIlixCwLNXKLoRCxZrmImM67UaBM3B0AkySFWBthhUUAtOGQ3PS5u9q97Y1v5Mbt66p7KXmIAiLAlHXUqKd07byvjZW7utiqupUM5KEyeahMHivrhLQX3ovStP_Qcvwwn_65P49zcHw</recordid><startdate>20200316</startdate><enddate>20200316</enddate><creator>Pan, Hui‐Jie</creator><creator>Hu, Xile</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-8335-1196</orcidid></search><sort><creationdate>20200316</creationdate><title>Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]‐Hydrogenase</title><author>Pan, Hui‐Jie ; Hu, Xile</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2027-ad5c3f0b4985677bb3c72f73446c1d451cdddda0ae6c720788906ce4f4f7007f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>[Fe]-Hydrogenase</topic><topic>Benzoxazines</topic><topic>Bioanorganische Chemie</topic><topic>Biomimetic materials</topic><topic>Biomimetics</topic><topic>Biomimetische Chemie</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>Hydrides</topic><topic>Hydrierung</topic><topic>Hydrogenase</topic><topic>Hydrogenation</topic><topic>Iron</topic><topic>Lewis acid</topic><topic>Mangan</topic><topic>Manganese</topic><topic>Mimicry</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pan, Hui‐Jie</creatorcontrib><creatorcontrib>Hu, Xile</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pan, Hui‐Jie</au><au>Hu, Xile</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]‐Hydrogenase</atitle><jtitle>Angewandte Chemie</jtitle><date>2020-03-16</date><risdate>2020</risdate><volume>132</volume><issue>12</issue><spage>4972</spage><epage>4976</epage><pages>4972-4976</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>[Fe]‐hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]‐hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]‐hydrogenase. This complex exhibits the highest activity and broadest scope in catalytic hydrogenation among known mimics. Thanks to its biomimetic nature, the complex exhibits unique activity in the hydrogenation of compounds analogous to methenyl‐H4MPT+, the natural substrate of [Fe]‐hydrogenase. This activity enables asymmetric relay hydrogenation of benzoxazinones and benzoxazines, involving the hydrogenation of a chiral hydride transfer agent using our catalyst coupled to Lewis acid‐catalyzed hydride transfer from this agent to the substrates.
Ein Mangan(I)‐Komplex, der nach dem Vorbild der [Fe]‐Hydrogenase entwickelt wurde, weist unter den bekannten biomimetischen Verbindungendie höchste Aktivität und den größten Reaktionsumfang für katalytische Hydrierungen auf. Durch seinen biomimetischen Charakter zeigt er insbesondere eine einzigartige Aktivität in der Hydrierung von analogen Verbindungen zu Methenyl‐H4MPT+, dem natürlichen Substrat der [Fe]‐Hydrogenase.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201914377</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8335-1196</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | [Fe]-Hydrogenase Benzoxazines Bioanorganische Chemie Biomimetic materials Biomimetics Biomimetische Chemie Catalysts Chemistry Coupling Hydrides Hydrierung Hydrogenase Hydrogenation Iron Lewis acid Mangan Manganese Mimicry Substrates |
| title | Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]‐Hydrogenase |
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