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Search for "biosynthesis" in Full Text gives 306 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA
Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35
- antibiotic properties, others expand the chemical diversity and thus the functional sophistication of ribonucleic acids, as in the case of Q [3]. In most bacteria, Q biosynthesis is tightly regulated by riboswitches, which are highly structured RNA elements located mostly in the 5’-leader of messenger RNA
- . PreQ1 riboswitches sense the cellular concentration of preQ1 and regulate the expression of downstream located genes associated with the biosynthesis or transport of Q in a feedback-like manner. Binding of PreQ1 to the mRNA causes the riboswitch to commit an altered folding pathway, which affects the
Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia
Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23
- spectrum to two sp3 carbon atoms at δC 67.8 (C-2') and 72.6 (C-3'), respectively. These results suggested that compound 1 possesses a tetramic acid moiety similar to prototenellin D (Figure 1), a precursor in the biosynthesis of tenellin [10], a 2-pyridone derivative purified from the entomopathogenic
- previously reported study investigating the biosynthesis of tenellin from Beauveria bassiana CBS110.25 [13], it was established that tenellin and a vast array of related metabolites could be synthesized through a cascade involving hybrid highly reducing polyketide synthase–non-ribosomal peptide synthetase
- (PKS–NRPS) [13]. Based on the structural relations between farinosones and tenellins differing only in the side chain length/the number of conjugated double bonds, farinosones were also postulated to be synthesized adopting a similar biosynthetic pathway. The biosynthesis of farinosones (Figure 4
Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina
Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267
- -labeled ʟ-phenylalanine [19]. Therefore, the cyano group in bromotyrosine alkaloids containing the phenylacetonitrile moiety is derived from the α-carbon and amino group of ʟ-tyrosine. On the other hand, the biosynthesis of nitrile with a cyanoformamide moiety remains unclear. Ceratinadin G (1) represents
- a rare nitrile that contains a cyano group as aminoacetonitrile. The biosynthesis of the 8,10-dibromo-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol scaffold has been proposed by Scheuer, Clardy and co-workers [5], but how the cyano group in 1 is biosynthesized remains unknown and is of
Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond
Beilstein J. Org. Chem. 2024, 20, 3050–3060, doi:10.3762/bjoc.20.253
- product biosynthesis, along with all the information an organism needs, are encoded in its genome. Genetic information is transcribed and translated into proteins that carry out chemical reactions that sustain life, which include both primary metabolism and the biosynthesis of natural products. Direct
- need to wait for enzymes to complete the entire course of biosynthesis, and then characterize chemical structure of the final natural product. While a generalized algorithm is not yet available, scientists in recent years have made some headways toward predicting the chemical structure of a natural
- silico to avoid rediscovery. They are the cornerstone of chemical structure metagenomics; a few examples in this area of research are described below. NRP biosynthesis and structure prediction NRPs are biosynthesized by either type I or II nonribosomal peptide synthetase (NRPS) [50][51]. Type I NRPS is a
Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines
Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236
- /ERG11 gene. This enzyme contains a haem-like prosthetic group in its active center and is a member of the cytochrome P450 family, which plays a key role in the biosynthesis of sterols. Sterols in turn are integral components of the fungal cell membrane, making inhibition of CYP51 [43] an effective
Young investigators in natural products chemistry, biosynthesis, and enzymology
Beilstein J. Org. Chem. 2024, 20, 2720–2721, doi:10.3762/bjoc.20.229
- . Their privileged structures have led organic and bioorganic chemists to develop methods to construct them. Our fundamental knowledge in enzymology is continually expanded by enzymes involved in natural products biosynthesis, as their production requires evolved enzymes to perform chemical reactions
- distinct from those seen in primary metabolism. Natural products have inspired generations of scientists and continue to do so today. This thematic issue highlights young investigators in natural products chemistry, biosynthesis, and enzymology. As early-career researchers ourselves, we are honored to
The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis
Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222
- gap between m/z 192 and 232 indicates a methyl group either at either C-5 or C-6. Taken together, the data from the derivatizations led to the conclusion that one methyl group is located at C-4 and a second at C-6. This is consistent with regular fatty acid biosynthesis of mid-chain methyl
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- fungi, are discussed with view on their isolation, structure, biological activities, biosynthesis, and total syntheses. This class of compounds consists until now of 127 naturally occurring compounds, with very divers structural motifs. Although only a handful of these toxins (i.e., alternariol and its
- interesting biological activities. Keywords: biosynthesis; fungal metabolites; polyketides; resorcylic lactones; total synthesis; Introduction Alternariol and some of its derivatives are ubiquitous as fungal metabolites present in infested plants and in food and feed, but similarly in soil, in wallpapers
- acid), whose biosynthesis is presumably starting from alternariol. The lactone moieties of these compounds are usually six-membered rings, where variations during or after polyketide synthesis occasionally give rise to five- or seven-membered rings or even to open structures with a free resorcylic acid
Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity
Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159
- spontaneously form in bovicin HJ50 to exert their natural activity and change spectra of antimicrobial effects when synthetically intramolecularly bound [17][18]. The biosynthesis of mature lanthipeptides involves the translation of lanA, which encodes a precursor peptide with two regions: a leader peptide that
- biosynthetic clusters or superclusters these precursor peptides belonged to contained all the genes lanA, lanM, and lanT. These genes were found to be the minimal machinery required for lanthipeptide biosynthesis (Figure 2). Notably, transporter genes and regulatory elements were not considered in the second
- filter as their presence is not needed for biosynthesis, albeit it is for resistance. As a result, the C. cellulovorans 743 clusters were chosen because they were thought to be complete, novel, and most interesting, primarily due to the presence of two different, apparently independent operons, each with
Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations
Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151
- approach" merging efficient enzymatic synthesis – traditionally employed in the biosynthesis of natural products by microorganisms and plants – with precise chemical synthesis conducted by chemists. Chemo-enzymatic total syntheses reported recently fall into three main categories based on the purpose for
- isolated from Alternaria brassicicola, a phytopathogenic fungus that causes dark leaf spots in Brassica species. The biosynthesis process of brassicicenes was primarily elucidated through in vitro enzymatic transformations and heterologous expression using Aspergillus oryzae. The proposed biosynthetic
- pathway of brassicicenes in Pseudocercospora fijiensis is outlined based on an investigation by Oikawa and co-workers [23]. The biosynthesis begins with the conversion of farnesyl pyrophosphate (FPP) and isopentenyl pyrophosphate (IPP) to geranylgeranyl pyrophosphate (GGPP), catalyzed by the
Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry
Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147
- within the context of ribosomally synthesised and post-translationally modified peptide (RiPP) natural products. Methyltransferases play a pivotal role in the biosynthesis of diverse natural products with unique chemical structures and bioactivities. They are highly chemo-, regio-, and stereoselective
- -translational modifications; ribosomal peptides; SAM-dependent enzymes; Introduction In the complex landscape of natural product biosynthesis, ribosomally synthesised and post-translationally modified peptides (RiPPs) stand out as a fascinating class of compounds with both structural diversity and unique
- encoded in the same BGC as the precursor peptide install post-translational modifications in the core peptide. Finally, a protease releases the modified core peptide, creating the mature natural product [2]. The transfer of a methyl group is a common post-translational modification in RiPP biosynthesis
Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty
Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146
- together with genes encoding the production of polybrominated pyrroles [138][139][140]. The Microbulbifer BGCs lack genes for brominated pyrrole biosynthesis and polybrominated pyrroles have not been reported to be produced by Microbulbifer bacteria. Future studies looking at the evolutionary relationship
- has been shared. Unlike the bulbiferamides mentioned above, the pseudobulbiferamides were not exclusively excreted out of the bacterial colonies. Biosynthesis The first genome sequence of a Microbulbifer bacterium was reported by Howard et al. in 2003 [117]. Now, more than 70 Microbulbifer genomes are
- typical Microbulbifer genome contains less than ten BGCs, as identified by antiSMASH, which implies that a large fraction of their genome is not devoted to natural product biosynthesis. The bulbiferamides and the pseudobulbiferamides represent the first and to date the only examples of peptidic natural
Mining raw plant transcriptomic data for new cyclopeptide alkaloids
Beilstein J. Org. Chem. 2024, 20, 1548–1559, doi:10.3762/bjoc.20.138
- -terminal Phe residue. Additional 663.3192 and 581.3345 m/z features were also present in the GNPS network, but MS/MS fragmentation could not definitively support a specific structure. For a better understanding of the biosynthesis of burpitides in G. jasminoides, we explored the genomic context by using
- base pairs (Figure 6B). While the proposed gene cluster is missing a potential peptidase, it contains all the other proteins necessary for the biosynthesis of GJA649 and the other putative G. jasminoides cyclopeptide alkaloids. New cyclopeptide alkaloids in Alternanthera bettzickiana Based on the
- precursor rulesets for the biosynthesis of this emerging class of plant natural products. Experimental Construction of precursor peptide HMM A custom hidden Markov model designed to target the precursor peptides from split burpitide pathways was created to favor producers of known burpitides. Sequences
Bioinformatic prediction of the stereoselectivity of modular polyketide synthase: an update of the sequence motifs in ketoreductase domain
Beilstein J. Org. Chem. 2024, 20, 1476–1485, doi:10.3762/bjoc.20.131
- : bioinformatics; conserved motifs; ketoreductase; polyketide synthase; stereocontrol; Introduction Type I modular polyketide synthases (PKSs) are large enzyme complexes that play a crucial role in the biosynthesis of bacterial polyketides, including many important clinical drugs such as erythromycin (antibiotic
- ) [3][4]. The building blocks for PKS biosynthesis often include malonyl-CoA or methylmalonyl-CoA, which are loaded onto the ACP by the AT domain. Subsequently, the KS domain catalyzes the decarboxylative Claisen condensation between the ACP-tethered extender unit and the KS-tethered growing chain. The
- stereoselectivity of a KR. Such promiscuity can also be observed in the MycA KR in mycolactone biosynthesis, which accepts both α-substituted and α-unsubstituted substrates while retaining the same stereoselectivity for the β-hydroxy group [28]. To further investigate the sequence features of each module type, we
Computation-guided scaffold exploration of 2E,6E-1,10-trans/cis-eunicellanes
Beilstein J. Org. Chem. 2024, 20, 1320–1326, doi:10.3762/bjoc.20.115
- ) of alkenes in the 10-membered ring (Figure 1A). During biosynthesis, the eunicellane skeleton is first constructed by terpene synthases that cyclize the diterpene precursor geranylgeranyl diphosphate (Figure 1B) [5][6][7][8][9]. The latter two structural elements, the configurations of the 6/10
- system and the C2–C3 alkene, are instilled by these terpene synthases. Four types of eunicellane synthases are known (Figure 1B). The first eunicellane synthase identified, Bnd4 from the biosynthesis of benditerpenoic acid in Streptomyces sp. (CL12-4) [5], forms a cis-eunicellane named benditerpetriene
- (1) [6]. In 1, the C2–C3 and C6–C7 alkenes are E-configured, with the latter alkene configuration being conserved in all known eunicellane cyclization mechanisms. The first trans-eunicellane synthase, AlbS from the biosynthesis of albireticulone in Streptomyces albireticuli [10], was also identified
Cofactor-independent C–C bond cleavage reactions catalyzed by the AlpJ family of oxygenases in atypical angucycline biosynthesis
Beilstein J. Org. Chem. 2024, 20, 1198–1206, doi:10.3762/bjoc.20.102
- Sciences, No. 1 Yanqihu East Road, Beijing 101408, China State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China 10.3762/bjoc.20.102 Abstract Biosynthesis of atypical angucyclines involves unique oxidative B-ring
- cofactor-independent manner. Keywords: angucyclines; aromatic polyketide; biosynthesis; cofactor-independent oxygenase; oxidative rearrangement reaction; Introduction The angucyclines represent a large class of natural products biosynthesized by type II polyketide synthases. Within this category, a
- cleavage and rearrangement in atypical angucycline biosynthesis are catalyzed by the AlpJ-family oxygenases, encompassing AlpJ, JadG, and GilOII. Biochemical analyses reveal the capability to transform the shared angucycline intermediate, dehydrorabelomycin (DHR, 1), into products with unique chemical
Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol
Beilstein J. Org. Chem. 2024, 20, 1189–1197, doi:10.3762/bjoc.20.101
- several significant processes, terpenoids play an indispensable role in cell-wall and membrane biosynthesis, sensing, plant defense, electron transport, or conversion of light into chemical energy [1][2]. Based on the number of hydrocarbon units, terpenes are classified into various families like
- germacrene A and hedycaryol and how this might affect product distribution in chemical synthesis and biosynthesis. Additionally, we compare the effect of the choice of DFT functional and basis set on the results. Methods The structures of all studied intermediate carbocations originating from germacrene A
- between the stability of hedycaryols (ΔΔEe) and C+···OH bond distances. Biosynthesis of (A) germacrene A and (B) hedycaryol from FPP. Here the abbreviations represent, FPP = farnesyl diphosphate, GAS = germacrene A synthase, OPP = diphosphate. O–C(cation) bond lengths (Å) in the hedycaryol cations
Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction
Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99
- inhibitory concentration (IC50) of 10 ng/mL, lepistatin A (3), along with two other new chlorinated analogs, that were isolated from Basidiomycete Lepista sordida culture, pauciflorol F (4), isolated from Vatica pauciflora, which is an important building block for the biosynthesis of bioactive polyphenols
Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines
Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94
- activity, such as antibacterial [8], anticancer [9] or antiproliferative [10]. In addition, isoxazolo[4,5-b]pyridines were found to inhibit cytochrome P450 CYP17 responsible for the biosynthesis of androgens and estrogen precursors [11]. Some biologically active isoxazolo[4,5-b]pyridines are shown on
A Diels–Alder probe for discovery of natural products containing furan moieties
Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88
- methylenomycin A. Specifically, an MMF binds to the TetR family transcriptional repressor (TFTR) resulting in the complex being released from the DNA ultimately allowing for gene transcription and production of enzymatic machinery necessary for the biosynthesis of methylenomycin A [6][7]. To date, there have
Enhancing structural diversity of terpenoids by multisubstrate terpene synthases
Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86
- Min Li Hui Tao Department of Otolaryngology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan, Hubei 430071, China Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, Wuhan University, Wuhan, Hubei 430071, China
- -methyltransferases, or engineered lepidopteran mevalonate pathways. The substrate promiscuity of TSs not only expands the structural diversity of terpenes but also highlights their potential for the discovery of novel terpenoids via combinatorial biosynthesis. In this review, we focus on the current knowledge on
- combinatorial biosynthesis. An important review published previously comprehensively addressed the transformation of synthetic prenyl-substrate analogs by TSs as well as TS-mimicking chemical transformations [13]. In this review, we discuss representative MSTSs originating from different species that use
Confirmation of the stereochemistry of spiroviolene
Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77
- stereochemistry by X-ray crystallography using a hydrazone derivative of 1. Results and Discussion Our work commenced with the heterologous production of spiroviolene by E. coli using a recently developed isopentenol utilization pathway for the efficient supply of two C5 precursors for terpene biosynthesis
Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria
Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75
- noursei, an NNG-producing bacterium, did not reveal any NnlA homologs. Interestingly, four NMOs are annotated in the S. noursei genome. These enzymes could protect S. noursei from NNG toxicity during its biosynthesis. Meanwhile, we posit that NnlA protects non-NNG producing bacteria from exposure. In vivo
Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus
Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73
- genome mining and heterologous expression, we identified a cav biosynthetic gene cluster responsible for the biosynthesis of DMTs 2–4, along with a P450, CavA, responsible for introducing the C-2 and C-3 hydroxy groups. Furthermore, the substrate scope of CavA revealed its ability to hydroxylate drimenol
- analogs. This discovery not only broadens the known chemical diversity of DMTs from bacteria, but also provides new insights into DMT biosynthesis in bacteria. Keywords: bacterial terpenoid; cytochrome P450s; drimane-type sesquiterpenoid; Streptomyces clavuligerus; terpenoid biosynthesis; Introduction
- emphasize the potential of DMTs as substances with broad and significant biological activities. The biosynthetic pathways for DMTs, especially for calidoustene C, (+)-isoantrocin, and (−)-antrocin, have been extensively elucidated [6][13][14][15][16][17][18][19][20] (Figure 1b). In the biosynthesis of
Methodology for awakening the potential secondary metabolic capacity in actinomycetes
Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69
- , and the associated undiscovered secondary metabolite biosynthesis genes are called “silent” genes. This review outlines several approaches to further activate the metabolic potential of actinomycetes. Keywords: actinomycete; co-culture; heat shock metabolites (HSMs); secondary metabolites; silent
- considered to have been completely characterized. This may be because the number of discovered compounds is small compared to the number of secondary metabolite biosynthesis genes harbored by actinomycetes [26][27][28]. For example, in Streptomyces avermitilis, 38 secondary metabolite biosynthetic gene
- identified. These as yet undiscovered secondary metabolite biosynthesis genes are called “silent genes”, because they are either not expressed or their expression levels are low under normal culture conditions. A number of studies have reported methods to activate these genes, and many new compounds have
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