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Biosynthesis of trialkyl-substituted aromatic polyketide NFAT-133 involves unusual P450 monooxygenase-mediating aromatization and a putative metallo-beta-lactamase fold hydrolase

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Synthetic and Systems Biotechnology 2023年第3期8卷 349-356页

作者： Ming Yang Wanlu Li Lin Zhou Xiao Lin Wenyu Zhang Yaoyao Shen Hai Deng Hou-wen Lin Yongjun Zhou Research Center for Marine Drugs Department of PharmacyRen Ji HospitalSchool of MedicineShanghai Jiao Tong UniversityShanghai200127China Institute of Marine Drugs Guangxi Key Laboratory of Marine DrugsGuangxi University of Chinese MedicineNanning530200PR China Department of Chemistry University of AberdeenAberdeenAB243UEUK

The bacterial trialkyl-substituted aromatic polyketides are structurally featured with the unusual aromatic core in the middle of polyketide chain such as TM-123(1),veramycin A(2),NFAT-133(3)and benwamycin I(4),which were discovered from Streptomyces species and demonstrated with antidiabetic and immunosuppressant activities.Though the biosynthetic pathway of 1-3 was reported as a type I polyketide synthase(PKS),the PKS assembly line was interpreted inconsistently,and it remains a mystery how the compound 3 was generated.Herein,the PKS assembly logic of 1-4 was revised by site-mutagenetic analysis of the PKS dehydratase domains.Based on gene deletion and complementation,the putative P450 monooxygenase nftE1 and metallo-beta-lactamase(MBL)fold hydrolase nftF1 were verified as essential genes for the biosynthesis of 1-4.The absence of nftE1 led to abolishment of 1-4 and accumulation of new products(5-8).Structural elucidation reveals 5-8 as the non-aromatic analogs of 1,suggesting the NftE1-catalyzed aromatic core formation.Deletion of nftF1 resulted in disappearance of 3 and 4 with the compounds 1 and 2 unaffected.As a rare MBL-fold hydrolase from type I PKSs,NftF1 potentially generates the compound 3 through two strategies:catalyze premature chain-offloading as a trans-acting thioesterase or hydrolyze the lactone-bond of compound 1 as an esterase.

关键词： Thioesterase Metallo hydrolase Metallo-beta-lactamase aromatic polyketide polyketide synthase P450 monooxygenase

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