A Streptomyces Cytochrome P450 Enzyme Catalyzes Regiospecific C2-Guaninylation for the Synthesis of Diverse Guanitrypmycin Analogs

Article Biochemistry & Molecular Biology

Genomics-Guided Efficient Identification of 2,5-Diketopiperazine Derivatives from Actinobacteria

Jing Liu et al.

Summary: Secondary metabolites derived from microorganisms play a crucial role in natural products. Genome mining and heterologous expression are efficient methods for discovering and studying novel metabolites.

CHEMBIOCHEM (2023)

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Article Chemistry, Physical

Biosynthesis of Guatrypmethine C Implies Two Different Oxidases for exo Double Bond Installation at the Diketopiperazine Ring

Lauritz Harken et al.

Summary: The study involved heterologous expression of a silent gene cluster from Streptomyces cinnamoneus which led to the identification of guatrypmethine C, a guaninylated cyclo-L-Trp-L-Met derivative with two exo double bonds at the diketopiperazine ring. Structural elucidation was achieved using MS, H-1, C-13, and N-15 NMR analyses including H-1-C-13 and H-1-N-15 HMBC. Gene combination and biochemical investigation confirmed that the formation of the two C=C bonds are catalyzed by two distinct enzyme families (i.e., cyclodipeptide oxidase and Fe-II/2OG-dependent oxygenase).

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Bromine Assisted MnO2 Dissolution Chemistry: Toward a Hybrid Flow Battery with Energy Density of over 300 Wh L-1

Yun Liu et al.

Summary: A novel catholyte based on a mixture of Mn2+ and Br- was proposed for high energy density and long cycle life flow batteries. The design allows the dead MnO2 to be fully discharged via a chemical-electrochemical reaction, resulting in high energy efficiency, energy density, and over 2000 cycles of continuous operation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Biotechnology & Applied Microbiology

Conversion of viridicatic acid to crustosic acid by cytochrome P450 enzyme-catalysed hydroxylation and spontaneous cyclisation

Jenny Zhou et al.

Summary: Cytochrome P450 monooxygenases (P450s) are versatile catalysts in regio- and stereoselective oxidation reactions, with TraB enzyme shown to be involved in the biosynthesis of crustosic acid by catalysing hydroxylation reaction. Gene deletion and heterologous expression studies confirmed the function of TraB in metabolite formation, aiding genetic manipulation in fungi.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2021)

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Article Plant Sciences

Elucidation of the Streptoazine Biosynthetic Pathway in Streptomyces aurantiacus Reveals the Presence of a Promiscuous Prenyltransferase/Cyclase

Jing Liu et al.

Summary: Heterologous expression of a three-gene cluster from Streptomyces aurantiacus led to the elucidation of the biosynthetic steps of streptoazine C. The prenyltransferase SasB showed high flexibility towards tryptophan-containing cyclodipeptides. This study provides potential use of enzymes with high substrate promiscuity for generating prenylated derivatives.

JOURNAL OF NATURAL PRODUCTS (2021)

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Review Biotechnology & Applied Microbiology

Modifications of diketopiperazines assembled by cyclodipeptide synthases with cytochrome P450 enzymes

Lauritz Harken et al.

Summary: 2,5-Diketopiperazines are the smallest cyclic peptides composed of two amino acids connected by two peptide bonds, which can be biosynthesized by different enzyme families in nature. Due to their stable scaffold, they can serve as precursors for various tailoring enzymes to generate intriguing secondary metabolites. Recent attention has been focused on cyclodipeptide synthase-associated P(450)s, as they can catalyze a wider range of reactions beyond oxidation.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2021)

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Review Biotechnology & Applied Microbiology

Natural products in drug discovery: advances and opportunities

Atanas G. Atanasov et al.

Summary: Natural products and their analogues have historically played a significant role in pharmacotherapy, however, they also present challenges. Recent technological and scientific developments are addressing these challenges and revitalizing interest in natural products as drug leads, particularly for combating antimicrobial resistance.

NATURE REVIEWS DRUG DISCOVERY (2021)

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Article Chemistry, Organic

Global Genome Mining Reveals a Cytochrome P450-Catalyzed Cyclization of Crownlike Cyclodipeptides with Neuroprotective Activity

Jessie James Limlingan Malit et al.

Summary: By conducting global genome mining of bacterial genomes, 829 cyclodipeptide biosynthesis gene clusters containing a cytochrome P450 gene were identified. Heterologous expression of these gene clusters led to the discovery of two novel crownlike cyclodipeptides, cyctetryptomycin A and B, which exhibit complex macrocycle structures and neuroprotective activity. Two cytochrome P450 enzymes catalyze sequential reactions resulting in the cyclization of diketopiperazine dimers within the gene clusters.

ORGANIC LETTERS (2021)

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Article Biotechnology & Applied Microbiology