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Heterochiral coupling in non-ribosomal peptide macrolactamization
| Title: | Heterochiral coupling in non-ribosomal peptide macrolactamization |
| Authors: | Matsuda, Kenichi Browse this author →KAKEN DB | | Zhai, Rui Browse this author | | Mori, Takahiro Browse this author | | Kobayashi, Masakazu Browse this author | | Sano, Ayae Browse this author | | Abe, Ikuro Browse this author | | Wakimoto, Toshiyuki Browse this author →KAKEN DB |
| Issue Date: | 4-May-2020 |
| Publisher: | Nature Publishing Group |
| Journal Title: | Nature Catalysis |
| Volume: | 3 |
| Start Page: | 507 |
| End Page: | 515 |
| Publisher DOI: | 10.1038/s41929-020-0456-7 |
| Abstract: | Heterochiral coupling is favoured in abiotic peptide bond formation, whereas biotic peptide bond formation is dominated by homochiral coupling. Here, we report that heterochiral coupling is a rather general paradigm in the head-to-tail macrolactamization of non-ribosomal peptide biosynthesis. The canonical cis-acting offloading cyclases, such as type I thioesterase (TE) and terminal condensation-like domains, catalyse head-to-tail macrolactamization between N- and C-terminal residues with d- and l-configurations, respectively. In contrast, the penicillin-binding protein-type TEs, a recently identified family of trans-acting cyclases, couple heterochiral residues with complementary stereoselectivity to the canonical one. Thus, a suite of cis- and trans-TE non-ribosomal peptide synthetases could overcome the stereochemical constraints present in heterochiral head-to-tail macrolactam formation in bacterial non-ribosomal peptide biosynthesis. Furthermore, we provide the structural rationale for the C-terminal stereoselectivity of non-canonical offloading cyclases. Penicillin-binding protein-type TEs with broad substrate specificity are potentially applicable as biocatalysts and genetic tools for synthetic biology. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/79676 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 脇本 敏幸
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