التفاصيل البيبلوغرافية
| العنوان: |
Reconstitution of a Highly Reducing Type II PKS System Reveals 6π-Electrocyclization Is Required for o ‑Dialkylbenzene Biosynthesis |
| المؤلفون: |
Jie Zhang (64655), Satoshi Yuzawa (1744645), Wei Li Thong (2229922), Tetsuro Shinada (1267575), Makoto Nishiyama (758947), Tomohisa Kuzuyama (1374678) |
| سنة النشر: |
2021 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biochemistry, Microbiology, Genetics, Developmental Biology, Infectious Diseases, Chemical Sciences not elsewhere classified, BGC, type II polyketide synthase system, Type II PKS System, biosynthetic gene cluster, biosynthetic scheme, ACP, intramolecular 6π- electrocyclization, 6 Z configuration, SANK, FAD, dialkylbenzene moiety, acyl carrier protein, dialkylbenzene moiety exhibit |
| الوصف: |
Natural products containing an o -dialkylbenzene moiety exhibit a wide variety of bioactivities, including antibacterial, antifungal, antitumor, and antiangiogenic activities. However, the biosynthetic scheme of the o -dialkylbenzene moiety remains unclear. In this study, we identified the biosynthetic gene cluster (BGC) of compounds 1 and 2 in Streptomyces sp. SANK 60404, which contains a rare o -dialkylbenzene moiety, and successfully reconstituted the biosynthesis of 1 using 22 recombinant enzymes in vitro. Our study established a biosynthetic route for the o -tolyl group within the o -dialkylbenzene moiety, where the triene intermediate 3 loaded onto a unique acyl carrier protein (ACP) is elongated by a specific ketosynthase–chain length factor pair of a type II polyketide synthase system with the aid of a putative isomerase to be termed “electrocyclase” and a thioesterase-like enzyme in the BGC. The C 2 -elongated all-trans diketo–triene intermediate is subsequently isomerized to the 6 Z configuration by the electrocyclase to allow intramolecular 6π-electrocyclization, followed by coenzyme FAD/FMN-dependent dehydrogenation. Bioinformatics analysis showed that the key genes are all conserved in BGCs of natural products containing an o -dialkylbenzene moiety, suggesting that the proposed biosynthetic scheme is a common strategy to form o -dialkylbenzenes in nature. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/journal_contribution/Reconstitution_of_a_Highly_Reducing_Type_II_PKS_System_Reveals_6_-Electrocyclization_Is_Required_for_i_o_i_Dialkylbenzene_Biosynthesis/13954936 |
| DOI: |
10.1021/jacs.0c13378.s001 |
| الاتاحة: |
https://doi.org/10.1021/jacs.0c13378.s001 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.30EA1C4D |
| قاعدة البيانات: |
BASE |