Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium
Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The e...
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Veröffentlicht in: | Tetrahedron 2024-03, Vol.154, p.133875, Article 133875 |
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creator | Le Viet, Lan Huong Tamura, Mayumi Matsuda, Tomoko |
description | Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The enzyme demonstrated a broad substrate compatibility with a variety of cyclic ketones. In addition, the preparative-scale reactions were successfully conducted, and the chiral lactones were obtained with yields of up to 91 % and enantiomeric excess (ee) values of up to 99 % (S).
[Display omitted]
•A green asymmetric synthetic method of chiral lactones was developed.•A Baeyer-Villiger monooxygenase from Fusarium sp. was used as a catalyst.•The reaction does not need explosive reagents; the oxidant is oxygen in the air.•Chiral lactones were obtained in up to 91 % isolated yield and up to ee 99 %(S). |
doi_str_mv | 10.1016/j.tet.2024.133875 |
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[Display omitted]
•A green asymmetric synthetic method of chiral lactones was developed.•A Baeyer-Villiger monooxygenase from Fusarium sp. was used as a catalyst.•The reaction does not need explosive reagents; the oxidant is oxygen in the air.•Chiral lactones were obtained in up to 91 % isolated yield and up to ee 99 %(S).</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2024.133875</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Baeyer villiger oxidation ; Chiral lactone ; enzymes ; fungi ; Fusarium ; lactones ; Monooxygenase ; oxidation ; oxygen ; Whole cell reaction</subject><ispartof>Tetrahedron, 2024-03, Vol.154, p.133875, Article 133875</ispartof><rights>2024 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c282t-f11fe70b5e129f74bf444d1e926afd07522c71cabdaf5faaa6f45db06ab497153</cites><orcidid>0000-0002-3165-239X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402024000553$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Le Viet, Lan Huong</creatorcontrib><creatorcontrib>Tamura, Mayumi</creatorcontrib><creatorcontrib>Matsuda, Tomoko</creatorcontrib><title>Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium</title><title>Tetrahedron</title><description>Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The enzyme demonstrated a broad substrate compatibility with a variety of cyclic ketones. In addition, the preparative-scale reactions were successfully conducted, and the chiral lactones were obtained with yields of up to 91 % and enantiomeric excess (ee) values of up to 99 % (S).
[Display omitted]
•A green asymmetric synthetic method of chiral lactones was developed.•A Baeyer-Villiger monooxygenase from Fusarium sp. was used as a catalyst.•The reaction does not need explosive reagents; the oxidant is oxygen in the air.•Chiral lactones were obtained in up to 91 % isolated yield and up to ee 99 %(S).</description><subject>Baeyer villiger oxidation</subject><subject>Chiral lactone</subject><subject>enzymes</subject><subject>fungi</subject><subject>Fusarium</subject><subject>lactones</subject><subject>Monooxygenase</subject><subject>oxidation</subject><subject>oxygen</subject><subject>Whole cell reaction</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kDtP5DAUhS0EEsPjB2zncpsMtuMkM9qKRcuChETBo7VunOsZj5x48HVg8-83aKipTvOdI52PsR9SLKWQ9dVumTEvlVB6Kcty1VRHbCF1rYtKy_qYLYTQotBCiVN2RrQTQkipygX7eBopgx-gDchhv08R7Ja7mPjWb7ZhKnCAIftIGNBm_46cpiFvkTzx6HgAm-OAxNuJA_8NOGEqXn0IfoOJ93GI8d-0mTcIuUux57cjQfJjf8FOHATCy688Zy-3f55v7oqHx7_3N9cPhVUrlQsnpcNGtBVKtXaNbp3WupO4VjW4TjSVUraRFtoOXOUAoHa66lpRQ6vXjazKc_bzsDs_exuRsuk9WQwBBowjmXJmatGsVDOj8oDaFIkSOrNPvoc0GSnMp2SzM7Nk8ynZHCTPnV-HDs4f3j0mQ9bjYLHzafZluui_af8HZa-IYw</recordid><startdate>20240325</startdate><enddate>20240325</enddate><creator>Le Viet, Lan Huong</creator><creator>Tamura, Mayumi</creator><creator>Matsuda, Tomoko</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-3165-239X</orcidid></search><sort><creationdate>20240325</creationdate><title>Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium</title><author>Le Viet, Lan Huong ; Tamura, Mayumi ; Matsuda, Tomoko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-f11fe70b5e129f74bf444d1e926afd07522c71cabdaf5faaa6f45db06ab497153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Baeyer villiger oxidation</topic><topic>Chiral lactone</topic><topic>enzymes</topic><topic>fungi</topic><topic>Fusarium</topic><topic>lactones</topic><topic>Monooxygenase</topic><topic>oxidation</topic><topic>oxygen</topic><topic>Whole cell reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le Viet, Lan Huong</creatorcontrib><creatorcontrib>Tamura, Mayumi</creatorcontrib><creatorcontrib>Matsuda, Tomoko</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le Viet, Lan Huong</au><au>Tamura, Mayumi</au><au>Matsuda, Tomoko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium</atitle><jtitle>Tetrahedron</jtitle><date>2024-03-25</date><risdate>2024</risdate><volume>154</volume><spage>133875</spage><pages>133875-</pages><artnum>133875</artnum><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The enzyme demonstrated a broad substrate compatibility with a variety of cyclic ketones. In addition, the preparative-scale reactions were successfully conducted, and the chiral lactones were obtained with yields of up to 91 % and enantiomeric excess (ee) values of up to 99 % (S).
[Display omitted]
•A green asymmetric synthetic method of chiral lactones was developed.•A Baeyer-Villiger monooxygenase from Fusarium sp. was used as a catalyst.•The reaction does not need explosive reagents; the oxidant is oxygen in the air.•Chiral lactones were obtained in up to 91 % isolated yield and up to ee 99 %(S).</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2024.133875</doi><orcidid>https://orcid.org/0000-0002-3165-239X</orcidid></addata></record> |
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subjects | Baeyer villiger oxidation Chiral lactone enzymes fungi Fusarium lactones Monooxygenase oxidation oxygen Whole cell reaction |
title | Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium |
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