Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• chemical structures of these lantibiotics make them promising candidates for treating drug-resistant pathogens, and the characterization of these compounds from Clostridium provides an opportunity to develop new antibiotics. Results and Discussion Genome mining of LanM enzymes’ sequence diversity to

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

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

• biological systems. The transferred methyl group is highlighted in grey. B) General reaction schemes of biological methylation reactions. Chemical structures of RiPPs with diverse O-, N-, C-, and S-methylations. Amino acids of lassomycin are shown in the three-letter code. For longipeptin A, the

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• distributions and origins of Microbulbifer bacteria strains, degradation enzymes, and secondary metabolite discoveries. A focus is placed on the novel chemical structures reported with reference to their biological activities and the biosynthetic studies they have inspired. Review Biopolymer degrading enzymes

• structures of sulfated polysaccharides κ-, ι-, and λ-carrageenans. Chemical structures of 4HBA (1) and parabens (2–14) isolated from Microbulbifer strains, and synthetic analogus (15–17). Chemical structures of nucleosides 18–20 isolated from Microbulbifer strains. Chemical structures of alkaloids 21–24

• isolated from Microbulbifer strains. Chemical structures of (2Z,4E)-3-methyl-2,4-decadienoic acid (25) and 4-BP (26) natural products isolated from Microbulbifer strains. Chemical structures of bulbiferamides 27–30 and pseudobulbiferamides 31–35. Proposed NRPS assembly lines for the biosynthesis of (A

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• @(12,2)-SWNT complexes. Chemical structures of Cu-tethered tetragonal nanobrackets 1a and 1b. Synthesis of nanobracket 4. Reaction conditions: i) XPhos Pd G2, XPhos, B2(OH)4, KOAc, EtOH, 80 °C, 2 h; ii) Br-Ar-Br, K2CO3, tetrahydrofuran (THF)/toluene, 80 °C, 16 h; iii) trifluoroacetic acid (TFA), pyrrole

Cofactor-independent C–C bond cleavage reactions catalyzed by the AlpJ family of oxygenases in atypical angucycline biosynthesis

• Jinmin Gao,
• Liyuan Li,
• Shijie Shen,
• Guomin Ai,
• Bin Wang,
• Fang Guo,
• Tongjian Yang,
• Hui Han,
• Zhengren Xu,
• Guohui Pan and
• Keqiang Fan

Beilstein J. Org. Chem. 2024, 20, 1198–1206, doi:10.3762/bjoc.20.102

• distinctive subset of compounds, including jadomycin, gilvocarcin, kinamycin, fluostatin, and lomaiviticin, arises from typical angucycline intermediates via oxidative C–C bond cleavage and subsequent ring rearrangement reactions. These atypical angucyclines exhibit intriguing chemical structures and various

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• , 2H), 9.34–9.36 (d, J = 8 Hz, 2H); 13C NMR (125 MHz, DMSO-d6 + TFA) δ 126.8, 127.8, 136.8, 138.3, 139.0, 147.9, 155.8; HRESIMS: [M + H]+ calcd for C16H8N6O2, 317.0787; found, 317.0776. Chemical structures of H-bonding N-heteroacenes synthesized by Miao et al. and Bunz et al. (a) [22][23]. Preparation

Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

• Dongxu Zhang,
• Wenyu Du,
• Xingming Pan,
• Xiaoxu Lin,
• Fang-Ru Li,
• Qingling Wang,
• Qian Yang,
• Hui-Min Xu and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73

• these, drimane-type sesquiterpenoids (DMTs) are distinct due to their chemical structures, which feature a decahydronaphthalene core adorned with methyl groups, mirroring the A/B rings found in labdane-derived diterpenoids [5][6] (Figure 1a). DMTs exhibit significant biological activities, such as those

• significant in industrial applications, renowned for its production of diverse natural products with chemical structures and bioactivities, such as cephamycin C, clavulanic acid, and isopenicillin N [22][23][24]. Genomic sequencing of S. clavuligerus has revealed 48 potential secondary metabolite BGCs, and

• ), 2α-hydroxydrimenol (3), and 3-ketodrimenol (4) (Figure 2a). HPLC analysis of metabolites from different culture media showed that YMS medium was more conducive to produce compound 3 (Figure 2b and Table S1 in Supporting Information File 1). The chemical structures of these isolated compounds were

Genome mining of labdane-related diterpenoids: Discovery of the two-enzyme pathway leading to (−)-sandaracopimaradiene in the fungus Arthrinium sacchari

• Fumito Sato,
• Terutaka Sonohara,
• Shunta Fujiki,
• Akihiro Sugawara,
• Yohei Morishita,
• Taro Ozaki and
• Teigo Asai

Beilstein J. Org. Chem. 2024, 20, 714–720, doi:10.3762/bjoc.20.65

• organizations were discovered, these enzymes would be useful to discuss and further analyze the evolution of TCs in fungi. LRDs in fungi. A) Chemical structures of representative fungal LRDs. B) Reactions catalyzed by selected fungal bifunctional TCs. Sequence analysis of AsPS and AsCPS. A) Biosynthetic gene

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• percent growth inhibition. (a) Chemical structures and (b) ESIMS/MS of variochelins A–E (1–5) isolated from Variovorax sp. H002. Parent ions are m/z 1075.08 [M + H]+ (1), m/z 1103.18 [M + H]+ (2), m/z 1047.06 [M + H]+ (3), m/z 1072.95 [M + H]+ (4), and m/z 1101.14 [M + H]+ (5). Parent ions are represented

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• found in the methods section. Chemical structures of compounds 1–12. Key 2D NMR correlations of compounds 1–3. Experimental and calculated ECD spectra at the CAM-B3LYP/6-311G(d,p) level of theory for compound 1. Biosynthetic exploration of compounds 1 and 2. A: The schematic presents the biosynthetic

Recent developments in the engineered biosynthesis of fungal meroterpenoids

• Zhiyang Quan and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

• molecular species withdraws a hydrogen atom, and the generated radical induces various reactions such as hydroxylation, unsaturation, epoxidation, halogenation, endoperoxidation, and C–C bond reconstruction, leading to the formation of diverse chemical structures [22][26][27][28][29][30][31]. Structure

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• . Optical density at 600 nm was read by a multi-detection microplate reader (Infinite M1000 Pro, Tecan). The human pathogenic bacteria and aquatic pathogenic strains were offered by the Institute of Oceanology, Chinese Academy of Sciences. Chemical structures of compounds 1–5 isolated from P. boydii CS-793

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

• Sharmila Neupane,
• Marcelo Rodrigues de Amorim and
• Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

• analyzed by LC–MS for comparison of the retention times. Structures of unguisins. Chemical structures of unguisin J (1) and unguisin B (2). Key gHMBC and gCOSY correlations, and NOESY interactions of 1. Clinker analysis of identified unguisin-encoding BGCs. UngE’ is a methyltransferase that methylates

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• spiro[indoline-3,5'-[1,2]diazepine]-6'-carboxylates 5a–g in 63–77% yields (Scheme 3). The substituents on both substrates also showed little effect on the yields. The chemical structures were fully characterized by HRMS, IR, 1H and 13C NMR spectra. For demonstrating the synthetic value of this protocol

• yields. The chemical structures of the spiro compounds 7a–n were established by various spectroscopy methods. In addition, the single crystal structure of compound 7a was also determined by X-ray diffraction (Figure 1). As can be seen from Figure 1, both the C–C and C–N double bonds are part of the

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• electrochemical potential scales. The CV technique provided detailed cyclic voltammograms, allowing us to analyze the redox behavior and electrochemical properties of the compounds under investigation. Chemical structures of pyridine-3,5-dicarbonitrile-based TADF emitters. Absorption (a, b) and PL (c, d) spectra

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• products and of the catalyst; t is the time of the reaction. Chemical structures of the molecular components used in this work: Co(II) complex 1 as the novel catalyst, the heteroleptic Cu(I) complex as photosensitizer, and the benzimidazolidine derivative BIH as the sacrificial electron donor. ORTEP

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• respective HOMO/LUMO level energies determined from CV E1/2 values. b) Corresponding CVs for PDIN-FB, PDIN-B, CN-PDIN-FB, and CN-PDIN-B with E1/2 values. a) Chemical structures of BHJ donor material PM6 and acceptor material Y6, b) conventional OPV device structure used in this study, and c) the work

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• couplings in PATs. Scheme 10 redrawn from [79]. General thiol-ene photopolymerization process. Scheme 11 redrawn from [81]. (a) Three generations of Grubbs catalysts. (b) Proposed mechanism for photo-ROMP via a reductive quenching pathway and (c, d) chemical structures of the (c) initiators and (d) monomers

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• -Diacetylalternariol (2): white amorphous powder, UV (MeOH): λmax (PDA): 222, 258, 330 nm; 1H NMR (500 MHz, DMSO-d6) and 13C NMR (125 MHz, DMSO-d6) are shown in Table 1; (+)-HRESIMS (m/z): [M + H]+ calcd for C18H15O7, 343.0812; found, 343.0809. Chemical structures of compounds 1 and 2. Key COSY and HMBC correlations

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• different reactivity to that of the adducts of 3-ethoxycarbonylmethyleneoxindoles. For confirming the chemical structures of dispirooxindoles 4a–i, the single crystal structure of compound 4a was determined by X-ray diffraction (Figure 2). In Figure 2, the two oxindole scaffolds are in trans-position. The

• -oxoindolin-3-ylidene)acetate with 5-chloro and 5-fluoro substituent gave the spiro compounds 3a–k in satisfactory yields. However, the dimedone adducts of ethyl 2-(2-oxoindolin-3-ylidene)acetate itself and its derivatives with 5-methyl group gave the products 3l and 3m in moderate yields. The chemical

• structures of the obtained dispiro compounds 3a–m were fully characterized by IR, HRMS, 1H and 13C NMR spectroscopy. Because of the three chiral carbon atoms in the product, several diastereomers might be formed in the reaction. However, TLC monitoring and 1H NMR spectra of the crude products clearly

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• prostate cancer cells PC-3) were obtained from the DSMZ collection (Braunschweig, Germany). Chemical structures of compounds 1–4. Key 1H,1H COSY, HMBC, and ROESY correlations of compounds 1 and 2. 1H and 13C NMR data of compounds 1 and 2 in methanol-d4. Supporting Information Supporting Information File

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• -dihydropyridines derived from the condensation of acetylacetone also afforded the expected product 4o in 65% yield. The chemical structures of the obtained isoquinoline[2,1-h][1,7]naphthyridines 4a–o were fully characterized by various spectroscopy methods and further confirmed by determination of the single

• ]pyrrole derivatives 6e, 6f, 6i, 6k, 6l, and 6m were isolated in 23–39% yield from the reaction mixture. In other cases, the corresponding 1,3a,4,6a-tetrahydrocyclopenta[b]pyrrole derivatives could not be isolated due to too low yields. By analyzing the chemical structures of the 1,3a,4,6a

• -tetrahydrocyclopenta[b]pyrrole derivatives 6, it was found that the 1,4-dihydropyridinyl ring of the substrate was converted to a fused pyrrole ring, which might be a result from a rearrangement process of the formed 2-azabicyclo[4.2.0]octa-3,7-diene-7,8-dicarboxylates 5a–o at elevated temperature. The chemical

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• the test organism. Ampicillin (Roth, Carl Roth GmbH + Co. KG, Germany), tetracycline (Fluka Honeywell International Inc., United States of America) and ciprofloxacin (Sigma, Sigma-Aldrich Chemie GmbH, Germany) were used as positive controls. Selected siderophores from β-proteobacteria. Chemical

• structures of compounds 1–6 isolated in this study and of the structurally related siderophores massiliachelin (7) and (S)-dihydroaeruginoic acid (8). 1H,1H-COSY and selected 1H,13C-HMBC correlations in 1. Proposed origin of the isolated compounds 1–6 as well as massiliachelin (7). Domain notation of the

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• ) Chemical structure of polyrotaxane 2; and (b) cartoon representation of the light-triggered degradation of rotaxane polymer 2 [52]. The key colour of the cartoon representation is analogous to that of the chemical structures. a) Chemical structures of rotaxanes (E)-3 and (Z)-3; b) stick representation of

• atoms. The key colour of the cartoon representation is analogous to that of the chemical structures. Stick representations of the solid structures of: (a) U-CB[8]-MPyVB showing an interlocked ligand connected to two uranium clusters; and (b) the intertwined photodimerized product within the crystalline

• : (i) FAIR open data from X-ray structures and Mercury® 2020.1 Software (Cambridge Crystallographic Data Center) to create Figures 1b (CCDC number 1943103), 3b (CCDC number 2018646) and 4 (CCDC numbers 2090727 and 2090729); (ii) chemical structures employing ChemBioDraw® Ultra 12.0 (CambridgeSoft

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• . In our studies of arthropods over the years, we have found that non-peptide small molecules play a significant role in chemical structures and biological activities [11][12][13][14][15][16]. In examining the chemical constituents of the millipede K. svenhedini, the focus was directed toward non