Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• against Gram-positive bacteria), will be conducted in our laboratory. Cyclization reactions to segetalins A–H, J and K. The CD spectra of segetalins A–H, J and K. Preparation of segetalins A–H, J and K. Preparation of linear peptides for segetalins A–H, J and K. Supporting Information Supporting

Pentacyclic aromatic heterocycles from Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles

• Kaylen D. Lathrum,
• Emily M. Hanneken,
• Katelyn R. Grzelak and
• James T. Fletcher

Beilstein J. Org. Chem. 2025, 21, 2524–2534, doi:10.3762/bjoc.21.194

• sharing structural similarity regarding N center placement showed antimicrobial activity, as measured by minimum inhibitory concentration assays. MIC values of 2–16 μM towards Gram-positive bacteria Staphylococcus epidermidis and Bacillus subtilis and 8–16 μM towards Saccharomyces cerevisiae yeast were

• counterparts 13–18. Because fused ring heterocycles are common components of bioactive molecules, a preliminary evaluation of toxicity for this newly defined class of compounds was completed. Antimicrobial potency against Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis, Gram-negative

• bacteria Escherichia coli and Klebsiella aerogenes, and yeast Candida albicans and Saccharomyces cerevisiae was determined using minimum inhibitory concentration (MIC) assays [55][56]. As summarized in Table 4, only five of the twenty-four compounds tested displayed an ability to suppress microbial growth

Effect of a photoswitchable rotaxane on membrane permeabilization across lipid compositions

• Udyogi N. K. Conthagamage,
• Lilia Lopez,
• Zuliah A. Abdulsalam and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2498–2512, doi:10.3762/bjoc.21.192

• bacteria or malignant cells like cancer) [5][6], or to influence membrane protein function and thereby control cellular behavior [7][8]. One promising approach is the development of light-activated molecules that can modulate membrane properties upon irradiation, enabling remote activation with high

The intramolecular stabilizing effects of O-benzoyl substituents as a driving force of the acid-promoted pyranoside-into-furanoside rearrangement

• Alexey G. Gerbst,
• Sofya P. Nikogosova,
• Darya A. Rastrepaeva,
• Dmitry A. Argunov,
• Vadim B. Krylov and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2025, 21, 2456–2464, doi:10.3762/bjoc.21.187

• ; stabilizing factors; Introduction Oligosaccharide chains bearing α-ᴅ-galactofuranosyl (Galf) units are widely distributed in nature. Thus such compounds were discovered in fungi and yeasts [1][2][3], bacteria [4][5][6][7], brown and green seaweeds [8][9], lichens [10], and other species [11]. The presence of

An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives

• Elizaveta V. Gradova,
• Nikita A. Ozhegov,
• Roman O. Shcherbakov,
• Alexander G. Tkachenko,
• Larisa Y. Nesterova,
• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183

• microorganisms was determined, including two fungal strains: Candida albicans ATCC 10231, C. albicans C1 – clinical strain, Gram-positive bacteria such as Staphylococcus aureus ATCC 25923, S. aureus ATCC 43300 (MRSA), Mycobacterium smegmatis ATCC 70084, and Gram-negative bacteria including Escherichia coli ATCC

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• -negative bacteria widely distributed in nature [41]. Some species within this genus produce lipases that effectively catalyze the desymmetrization of prochiral diols, which were used in total syntheses. In 2003, an enzymatic asymmetric acylation with PSA, a lipase from Pseudomonas cepacia, was adopted by

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• Gram-negative bacteria. 2.3 Enzyme-responsive controlled release Elevated enzyme levels often mark the microenvironment of many pathological tissues, as well as intracellular and cellular compartments. These enzymes can serve as effective triggers for drug release in stimulus-responsive systems. Owing

Approaches to stereoselective 1,1'-glycosylation

• Daniele Zucchetta and
• Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

• mixtures of anomers and are therefore problematic to use in chemical glycosylation reactions. Keywords: carbohydrates; chemical glycosylation; Introduction Nonreducing disaccharides are abundant components of non-mammalian glycans and glycolipids found in fungi [1], nematodes [2], and bacteria such as

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

• Tsun-Yi Chiang,
• Mei-Huei Lin,
• Chun-Wei Chang,
• Jinq-Chyi Lee and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

• ; pyruvate ketals; Introduction Pyruvate ketals are essential non-carbohydrate modifications in polysaccharides from bacteria and serve as a key immunodominant group with many biological functions [1]. For example, the pyruvylated galactose moiety is a key component of Bacteroides fragilis capsular

• to synthesize a pyruvate ketal-containing PS A1 precursor associated with the commensal anaerobic bacteria capsule (Scheme 1) [7][8][9][10][11]. The target structure was β-ᴅ-Galf-(1→3)-α-ᴅ-Gal-(1→3)-β-ᴅ-Gal. This molecule acts as a critical intermediate for synthesizing various O4-linked PS A1

Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids

• Ye Yuan,
• Zhenhua Guan,
• Xue-Jie Zhang,
• Nanyu Yao,
• Wenling Yuan,
• Yonghui Zhang,
• Ying Ye and
• Zheng Xiang

Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111

• biosynthesis; P450 oxidation; synthesis; Introduction Fusicoccanes are a family of 5-8-5 tricyclic diterpenoid natural products that are produced by bacteria, fungi, algae, and plants (Figure 1a) [1][2][3][4][5][6][7]. Fusicoccanes possess a broad range of biological activities, including anticancer, anti

N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B

• Joy E. Rajakulendran,
• Emmanuel Tope Oluwabusola,
• Michela Cerone,
• Terry K. Smith,
• Olusoji O. Adebisi,
• Adefolalu Adedotun,
• Gagan Preet,
• Sylvia Soldatou,
• Hai Deng,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103

• bacteria, especially in the acquisition of nutrients [2], establishment of virulence [3][4][5][6], and defence against predators and competitors [7][8]. One such class of secondary metabolites are the siderophores [9][10][11] which are structurally diverse low molecular weight secondary metabolites

Synthetic approach to borrelidin fragments: focus on key intermediates

• Yudhi Dwi Kurniawan,
• Zetryana Puteri Tachrim,
• Teni Ernawati,
• Faris Hermawan,
• Ima Nurasiyah and
• Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

• County, Sichuan Province, China, along with other borrelidin derivatives, including borrelidin E (Table 1, entry 8) and 12-desnitrile-12-carboxyborrelidin (Table 1, entry 19) [23]. The latter compound, found in both endophytic bacteria and as a product of borrelidin biosynthesis, contributed to the

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• -waste [21], or to acidophilic microbes such as chemolithotrophic bacteria and archaea, which can accelerate the oxidative dissolution of gold sulfides in a biotechnological extraction process suited for sulfidic ores [22]. Microbial leaching methods are not, however, implemented at the industrial scale

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• eliminate invading bacteria via the inhibition of metabolic enzymes and DNA destruction. However, overexpression of iNOS results in the overproduction of NO which is associated with septic shock and tissue damage [6]. Therefore, inhibition of iNOS could be considered a potential therapeutic strategy for

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

• Leon M. Friedrich and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

• adhesion. We have investigated type 1 fimbriae-mediated adhesion of Escherichia coli (E. coli) bacteria, a process that is fundamental to UPEC (uropathogenic E. coli) infections [25]. Type 1 fimbriae are adhesive organelles projecting from the bacterial surface and are terminated by the lectin FimH, which

• relationships between ligand orientation and anti-adhesive properties of the respective inhibitor. Biological testing For the adhesion-inhibition assays, type-1-fimbriated E. coli bacteria were employed where the α-ᴅ-mannoside-specific adhesion is mediated by the fimbrial lectin FimH. According to a known

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

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

• naturally in mRNA riboswitches in bacteria and is involved in ligand-dependent gene regulation. Therefore, this riboswitch (like others) has become an attractive target for drug design. To date, most known RNA–small molecule binders interact in a non-covalent manner. The compounds presented here are part of

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• 2656), Schizosaccharomyces pombe (DSM 70572), Rhodotorula glutinis (DSM 10134), and Wickerhamomyces anomalus (DSM 6766). Additionally, various Gram-positive bacteria such as Staphylococcus aureus (DSM 346), Bacillus subtilis (DSM 10), Mycobacterium smegmatis (ATCC 700084), and Gram-negative bacteria

• including Acinetobacter baumannii (DSM 30008), Escherichia coli (DSM 1116), Chromobacterium violaceum (DSM 30191), and Pseudomonas aeruginosa (PA14) were included in the assessment. Gentamicin and nystatin served as positive controls against most bacteria and all fungi, respectively. For specific

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• antibacterial agents [20][21]. The absence of polyamine chains in ianthelliformisamines D–G (4–7) could explain the loss of activity seen in our assessment against P. aeruginosa. The synthetic molecule of 7 has been tested by other researchers against Gram-negative bacteria including P. aeruginosa with reported

• /461/463 [M + H]+. Bacterial strains and media Wild-type Pseudomonas aeruginosa strain PAO1 (prototrophic wild-type) [25] was used in this study. Bacteria were grown in Luria–Bertani (LB) medium (10 g/L tryptone, 10 g/L sodium chloride and 5 g/L yeast extract). Biofilm inhibition assay The overnight

• ) and diluted to an OD600 of 0.01. Test compounds (15 µL) were loaded prior to the addition of bacteria (135 µL) into 96-well plates. The plates were incubated for 24 h at 37 °C in static conditions. The effects of compounds on bacterial growth and the viability of biofilm bacteria was determined by the

Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond

• Thomas Ma and
• John Chu

Beilstein J. Org. Chem. 2024, 20, 3050–3060, doi:10.3762/bjoc.20.253

• based on a dataset of known pairs of nonribosomal code/substrate BB. c) An analysis that compared the known vs predicted NRP BBs grouped based on their chemical structures found both oversampled (green)/underexplored (blue) niches in the NRP chemical space; the analysis was performed across all bacteria

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• contamination with the strongly mutagenic altertoxins [82][83]. When administered to rats, AME induced gene mutations, chromosome breakage, and DNA damage [114]. AME turned out to be active against bacteria (Bacillus subtilis, Staphylococcus haemolyticus, Agrobacterium tumefaciens, Pseudomonas lachrymans

• , and 1.7 μM, respectively) [160], and further bacteria [164] and showed antimicrobial activity against Trypanosoma brucei rhodesiense, Leishmania donovani, and Plasmodium falciparum (IC50: 13.6, 7.5, 28.3 µM) [159]. It was cytotoxic against soybean cell cultures with an EC50 value of 0.63 µM [158] and

• ), Bacillus cereus (MIC values of 8–32 μg/mL [187][193], and further bacteria [163]. It turned out to be active against Trypanosoma brucei rhodesiense and Leishmania donovani (IC50 values of 1.5, 7.1 μM, respectively) and further protozoa [159]. It furthermore showed some radical scavenging activities [163

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• in bacteria, which are able to use most of the mammalian sugar units to construct their glycoconjugates but, in addition, can also use a wide variety of particular, and potentially endless, monosaccharides that are instead not present in eukaryotes (Figure 2). This huge diversity and complexity

2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• thiohistidine (89) were evaluated for skincare anti-inflammatory properties by Brancaccio et al. (Scheme 12) [64]. These compounds, biosynthesized by microalgae, bacteria and marine invertebrates feature skin protection via Nrf2 activation (nuclear factor erythroid 2-related factor 2). Antimalarial properties

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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

• of the purified lanthipeptide were confirmed by MS–MS/MS analysis for cellulosin, while clostrisin was not post-translationally modified. Both peptides demonstrated antimicrobial activity against multidrug-resistant bacteria, such as a clinical strain of Staphylococcus epidermidis MIQ43 and

• associated bioactive peptides. Keywords: antimicrobials; genome mining; lantibiotics; lanthipeptides; multi-drug resistant bacteria; natural products; Introduction Antimicrobial resistance (AMR) is a significant public health challenge. Only in 2019, there were 4.95 million deaths associated with AMR [1

• . Furthermore, the increasing availability of genomic data has led to the development of bioinformatics tools, such as AntiSMASH [3], Bagel4 [4], and RiPPMiner [5], that have emerged to streamline the process of exploring and discovering BGCs in bacteria, known as genome mining. Genome mining has emerged as a

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• , while antibacterial activity was tested against Gram-positive and Gram-negative bacteria. Unfortunately, all compounds exhibited very low activity in these assays. However, the oxathiaphospholanes were evaluated for their antifungal properties against Candida albicans and Saccharomyces cerevisiae, where