Themed collection Biosynthesis
Dehydroamino acids: chemical multi-tools for late-stage diversification
α,β-Dehydroamino acids (dhAAs) are noncanonical amino acids that are found in a wide array of natural products and can be easily installed into peptides and proteins.
Org. Biomol. Chem., 2019,17, 3653-3669
https://doi.org/10.1039/C8OB03155J
The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases
Tailoring enzymes decorate diketopiperazines to yield unique structures and biological functions.
Org. Biomol. Chem., 2019,17, 2305-2314
https://doi.org/10.1039/C8OB03063D
Biosynthesis of bioactive natural products from Basidiomycota
The club fungi, Basidioycota, produce a wide range of bioactive compounds. Here, we describe recent studies on the biosynthetic pathways and enzymes of bioactive natural products from these fungi.
Org. Biomol. Chem., 2019,17, 1027-1036
https://doi.org/10.1039/C8OB02774A
Active site labeling of fatty acid and polyketide acyl-carrier protein transacylases
Fluorescent probe design and site-directed mutagenesis unveil new activity-based chemical reporters for fatty acid and polyketide synthase acyl-carrier protein transacylases.
Org. Biomol. Chem., 2019,17, 4720-4724
https://doi.org/10.1039/C8OB03229G
Chorismatases – the family is growing
A newly discovered subfamily of chorismatases catalyses the same reaction as chorismate lyases (cleavage of chorismate to 4-hydroxybenzoate), but does not suffer from product inhibition.
Org. Biomol. Chem., 2019,17, 2092-2098
https://doi.org/10.1039/C8OB03038C
Seven-enzyme in vitro cascade to (3R)-3-hydroxybutyryl-CoA
Economical and environmentally-friendly routes to convert feedstock chemicals like acetate into valuable chiral products such as (R)-3-hydroxybutyrate are in demand.
Org. Biomol. Chem., 2019,17, 1375-1378
https://doi.org/10.1039/C8OB02858C
SurE is a trans-acting thioesterase cyclizing two distinct non-ribosomal peptides
A new stand-alone thioesterase, SurE, is capable of offloading two different NRPS assembly lines to generate two structurally unrelated cyclopeptides.
Org. Biomol. Chem., 2019,17, 1058-1061
https://doi.org/10.1039/C8OB02867B
Functional characterization of the halogenase SpmH and discovery of new deschloro-tryptophan dimers
Inactivation of the halogenase gene spmH led to discovery of four new deschloro-tryptophan dimers. SpmH was further biochemically characterized in vitro as an L-tryptophan 5-halogenase.
Org. Biomol. Chem., 2019,17, 1053-1057
https://doi.org/10.1039/C8OB02775G
Use of plant hormones to activate silent polyketide biosynthetic pathways in Arthrinium sacchari, a fungus isolated from a spider
A new method to activate fungal silent biosynthesis by using natural and synthetic plant hormones.
Org. Biomol. Chem., 2019,17, 780-784
https://doi.org/10.1039/C8OB02837K
Biosynthesis of the uridine-derived nucleoside antibiotic A-94964: identification and characterization of the biosynthetic gene cluster provide insight into the biosynthetic pathway
The biosynthetic pathway of the uridine-derived nucleoside antibiotic A-94964 was proposed via in silico analysis coupled with gene deletion experiments.
Org. Biomol. Chem., 2019,17, 461-466
https://doi.org/10.1039/C8OB02765J
In vitro reconstitution of the biosynthetic pathway of 3-hydroxypicolinic acid
Four enzymes direct the biosynthesis of 3-hydroxypicolinic acid, an important building block of bacterial natural products.
Org. Biomol. Chem., 2019,17, 454-460
https://doi.org/10.1039/C8OB02972E
Biosynthesis of an anti-tuberculosis sesterterpenoid asperterpenoid A
Biosynthesis of a potent MptpB inhibitor asperterpenoid A by a sesterterpene cyclase AstC and a multifunctional P450 enzyme AstB.
Org. Biomol. Chem., 2019,17, 248-251
https://doi.org/10.1039/C8OB02832J
Biosynthesis of lagopodins in mushroom involves a complex network of oxidation reactions
Targeted gene knockout in Coprinopsis cinerea, yeast in vivo bioconversion and in vitro assays elucidated the lagopodin biosynthetic pathway, including a complexity-generating network of oxidation steps.
Org. Biomol. Chem., 2019,17, 234-239
https://doi.org/10.1039/C8OB02814A
Heterologous production of asperipin-2a: proposal for sequential oxidative macrocyclization by a fungi-specific DUF3328 oxidase
A heterologous production of asperipin-2a and determination of its absolute structure revealed a sequential oxidative cyclization catalyzed by DUF3328 oxidase.
Org. Biomol. Chem., 2019,17, 39-43
https://doi.org/10.1039/C8OB02824A
Directed production of aurantizolicin and new members based on a YM-216391 biosynthetic system
Aurantizolicin and new compound 3 with improved bioactivity were generated highly effectively by heterologous expression of an engineered YM-216391 biosynthetic gene cluster.
Org. Biomol. Chem., 2018,16, 9373-9376
https://doi.org/10.1039/C8OB02665C
StnK2 catalysing a Pictet–Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin
StnK2 is a new Pictet–Spenglerase specifically catalyzing a (1R,3S,4S)-tetrahydro-β-carboline scaffold as the biosynthetic intermediate of the antitumor reagent streptonigrin.
Org. Biomol. Chem., 2018,16, 9124-9128
https://doi.org/10.1039/C8OB02710B
Deletion of a global regulator LaeB leads to the discovery of novel polyketides in Aspergillus nidulans
By disruption of LaeB, a global regulator recently characterized in Aspergillus nidulans, eight cryptic compounds in the mutant were identified, including seven polyketides and one NRPS-like product.
Org. Biomol. Chem., 2018,16, 4973-4976
https://doi.org/10.1039/C8OB01326H
Characterization of MtdV as a chorismate lyase essential to A201A biosynthesis and precursor-directed biosynthesis of new analogs
MtdV is a chorismate lyase involved in converting chorismate to 4HB, a vital precursor of A201A; precursor-directed biosynthesis enabled production of new A201A analogs.
Org. Biomol. Chem., 2019,17, 3760-3764
https://doi.org/10.1039/C8OB02852D
Synthesis, bioactivity, and enzymatic modification of antibacterial thiotetromycin derivatives
Interrogating the bioactivities and enzymatic modification potential of a focused library of novel synthetic thiotetronate compounds.
Org. Biomol. Chem., 2019,17, 3416-3423
https://doi.org/10.1039/C8OB03109F
Mechanistic characterization of three sesquiterpene synthases from the termite-associated fungus Termitomyces
Three terpene synthases from the termite associated fungus Termitomyces were studied by isotopic labelling experiments and site-directed mutagenesis.
Org. Biomol. Chem., 2019,17, 3348-3355
https://doi.org/10.1039/C8OB02744G
Biosynthetic studies of novel polyketides from the marine sponge-derived fungus Stachylidium sp. 293K04
A methylation of the acetate starter unit is part of the polyketide biosynthesis of phthalides and phthalimidines from the marine-derived fungus Stachylidium sp. 293K04.
Org. Biomol. Chem., 2019,17, 2747-2752
https://doi.org/10.1039/C9OB00198K
Identification of the common biosynthetic gene cluster for both antimicrobial streptoaminals and antifungal 5-alkyl-1,2,3,4-tetrahydroquinolines
The new subfamily of type II PKS gene cluster is responsible for biosynthesis of structurally distinct streptoaminals (STAMs) and 5-alkyl-1,2,3,4-tetrahydroquinolines (5aTHQs).
Org. Biomol. Chem., 2019,17, 2370-2378
https://doi.org/10.1039/C8OB02846J
Characterization of the flavin monooxygenase involved in biosynthesis of the antimalarial FR-900098
An amine hydroxylase catalyzes a latter step in the biosynthesis of the antimalarial FR900098.
Org. Biomol. Chem., 2019,17, 1506-1518
https://doi.org/10.1039/C8OB02840K
Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase
Aza-analogues of carbocations inhibit δ-cadinene synthase: 1,6-cyclisation.
Org. Biomol. Chem., 2019,17, 1206-1214
https://doi.org/10.1039/C8OB02821D
Probing the limits of interrupted adenylation domains by engineering a trifunctional enzyme capable of adenylation, N-, and S-methylation
The adenylation (A) domains found in nonribosomal peptide synthetases (NRPSs) exhibit tremendous plasticity.
Org. Biomol. Chem., 2019,17, 1169-1175
https://doi.org/10.1039/C8OB02996B
Use of the dehydrophos biosynthetic enzymes to prepare antimicrobial analogs of alaphosphin
An efficient method for preparing phosphonodipeptides, compounds that have potential as clinical antibiotics, is reported using enzymatic catalysis.
Org. Biomol. Chem., 2019,17, 822-829
https://doi.org/10.1039/C8OB02860E
Characterization of the N-methyltransferases involved in the biosynthesis of toxoflavin, fervenulin and reumycin from Streptomyces hiroshimensis ATCC53615
Four SAM-dependent N-methyltransferases are involved in the biosynthesis of toxoflavin, fervenulin, and reumycin from Streptomyces hiroshimensis ATCC53615.
Org. Biomol. Chem., 2019,17, 477-481
https://doi.org/10.1039/C8OB02847H
pH-Rate profiles establish that polyketide synthase dehydratase domains utilize a single-base mechanism
PKS dehydratases utilize a one-base mechanism.
Org. Biomol. Chem., 2018,16, 9165-9170
https://doi.org/10.1039/C8OB02637H
Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway
Enzymatic activity and crystal structures of the methyltransferases involved in the biosynthesis of fungal natural products meleagrin and oxaline.
Org. Biomol. Chem., 2018,16, 6450-6459
https://doi.org/10.1039/C8OB01565A
About this collection
This themed collection, Guest Edited by Professor Ikuro Abe, Professor Jeroen S. Dickschat, Professor Wenjun Zhang and Professor Taifo Mahmud, is a forum for the dissemination of cutting edge research on a range of topics related to the biogenesis of natural products. This will include genome mining and elucidation of biosynthetic pathway, mechanistic studies on natural product biosynthesis, studies of the genes and enzymes involved in natural product biosynthesis, enzyme engineering and biocatalysis and metabolic engineering for synthetic biology.
Articles in this themed collection will be added below as soon as possible after they are published.
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