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Discovery and Biosynthesis of Cihunamides, Macrocyclic Antibacterial RiPPs with a Unique C-N Linkage Formed by CYP450 Catalysis
DC Field | Value | Language |
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dc.contributor.author | An, Joon Soo | - |
dc.contributor.author | Lee, Hyunbin | - |
dc.contributor.author | Kim, Hyungyu | - |
dc.contributor.author | Woo, Seungyeon | - |
dc.contributor.author | Nam, Hyunsung | - |
dc.contributor.author | Lee, Jayho | - |
dc.contributor.author | Lee, Ji Yun | - |
dc.contributor.author | Nam, Sang-Jip | - |
dc.contributor.author | Lee, Sang Kook | - |
dc.contributor.author | Oh, Ki-Bong | - |
dc.contributor.author | Kim, Seok Hee | - |
dc.contributor.author | Oh, Dong Chan | - |
dc.date.accessioned | 2024-08-08T01:20:53Z | - |
dc.date.available | 2024-08-08T01:20:53Z | - |
dc.date.created | 2023-06-05 | - |
dc.date.created | 2023-06-05 | - |
dc.date.issued | 2023-06 | - |
dc.identifier.citation | Angewandte Chemie International Edition, Vol.62 No.26, p. 2023100998 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | https://hdl.handle.net/10371/205269 | - |
dc.description.abstract | Cihunamides A-D (1-4), novel antibacterial RiPPs, were isolated from volcanic-island-derived Streptomyces sp. The structures of 1-4 were elucidated by H-1, C-13, and N-15 NMR, MS, and chemical derivatization; they contain a tetrapeptide core composed of WNIW, cyclized by a unique C-N linkage between two Trp units. Genome mining of the producer strain revealed two biosynthetic genes encoding a cytochrome P450 enzyme and a precursor peptide. Heterologous co-expression of the core genes demonstrated the biosynthesis of cihunamides through P450-mediated oxidative Trp-Trp cross-linking. Further bioinformatic analysis uncovered 252 homologous gene clusters, including that of tryptorubins, which possess a distinct Trp-Trp linkage. Cihunamides do not display the non-canonical atropisomerism shown in tryptorubins, which are the founding members of the "atropitide" family. Therefore, we propose to use a new RiPP family name, "bitryptides", for cihunamides, tryptorubins, and their congeners, wherein the Trp-Trp linkages define the structural class rather than non-canonical atropisomerism. | - |
dc.language | 영어 | - |
dc.publisher | John Wiley & Sons Ltd. | - |
dc.title | Discovery and Biosynthesis of Cihunamides, Macrocyclic Antibacterial RiPPs with a Unique C-N Linkage Formed by CYP450 Catalysis | - |
dc.type | Article | - |
dc.identifier.doi | 10.1002/anie.202300998 | - |
dc.citation.journaltitle | Angewandte Chemie International Edition | - |
dc.identifier.wosid | 000986214300001 | - |
dc.identifier.scopusid | 2-s2.0-85159067671 | - |
dc.citation.number | 26 | - |
dc.citation.startpage | 2023100998 | - |
dc.citation.volume | 62 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Lee, Sang Kook | - |
dc.contributor.affiliatedAuthor | Kim, Seok Hee | - |
dc.contributor.affiliatedAuthor | Oh, Dong Chan | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | ABSOLUTE-CONFIGURATION | - |
dc.subject.keywordPlus | AMINO-ACIDS | - |
dc.subject.keywordPlus | CYTOCHROME-P450 | - |
dc.subject.keywordPlus | PEPTIDE | - |
dc.subject.keywordPlus | ASSIGNMENT | - |
dc.subject.keywordPlus | MECHANISM | - |
dc.subject.keywordPlus | REVEALS | - |
dc.subject.keywordAuthor | Antibacterial Natural Products | - |
dc.subject.keywordAuthor | Biosynthesis | - |
dc.subject.keywordAuthor | Cytochrome P450 Enzymes | - |
dc.subject.keywordAuthor | RIPPs | - |
dc.subject.keywordAuthor | Structural Elucidation | - |
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