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

• and sometimes also similar depending on the isomeric state (E or Z) of the azobenzene hinge, regardless of whether the second antenna projects a glucose (1) or a mannose (2) moiety. Whereas in compounds 4 and 5, the E isomers show higher binding energies, in the heterobivalent glycocluster 6βGlc3αMan

• with FimH (Supporting Information File 1, Figures S19–S21). In addition to the π–π interaction of the CRD-bound mannose-projecting antenna of the EE isomer with Tyr48, the complex is stabilized by hydrogen bonds of the scaffold mannoside to Tyr48 and in case of the glucose moiety to Thr51, Ile52, and

• Thr53. The high binding energy of the ZZ isomer, on the other hand, can be explained by additional hydrogen bonds of the scaffold mannoside to Asn138 and Ser139 (but not to Tyr48) and furthermore, the glucose moiety interacts with Arg92, Asn135, Asn138, and Asp140. The binding energies predicted for the

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

• Christian Akakpo,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

• [n])), and those prepared by metal ligands and H-bonding self-assembly processes [1][2][10][11][12][13][14][15][16][17][18][19][20]. Macrocycles have played key roles in important real-world products including the household deodorizer FebreezeTM, glucose monitors, and as solubilizing excipients [21

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• three human cancer cell lines, namely A549, Hs683, and SKMEL-28 with IC50 of 32.9, 31.5, and 35.2 μM, respectively [15]. Recently, we discovered that massarilactone D was the main secondary metabolite produced during shake flasks fermentation in YMG medium (1.0% malt extract, 0.4% glucose, 0.4% yeast

Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether

• Gianpaolo Gallo and
• Bartosz Lewandowski

Beilstein J. Org. Chem. 2025, 21, 541–546, doi:10.3762/bjoc.21.42

• binding of tryptophan is therefore important for diagnostic and medicinal applications. Recently, we reported a glucose naphtho crown ether which is a chemoselective receptor for the esters of aromatic amino acids, in particular tryptophan, in water. Herein, we demonstrate that the same compound also

• binds free tryptophan selectively in aqueous media. Furthermore, it is capable of binding to tryptophan within model tripeptides. The naphthalene functionality in the glucose-derived receptor enables the study of guest binding using fluorescence spectroscopy. Keywords: amino acids; macrocyclic

• aqueous media is limited (Figure 1a–c) [13][14][15][16][17][18]. In particular, receptors which bind tryptophan residues in peptides are rare [19][20]. Recently, we developed a glucose-based naphtho crown ether 1 (Figure 1d) which binds amino acid methyl esters with aromatic side chains chemoselectively

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

• shaking, and absorbance was measured at 490 nm (Synergy 2, BioTek). Error bars indicate SD with duplicates in two biological repeats (n = 4). Growth curve of S. aureus The growth of S. aureus (DSM 1104) was studied in CASO with 4% glucose and Mueller–Hinton broth (MHB), following a previously described

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• Synthesis and structure of cyclodextrin-based (poly)rotaxanes CDs are cyclic sugar molecules in which multiple glucose units that are connected by α-1,4 bonds, e.g., α-CD, β-CD, and γ-CD (glucose-unit numbers 6, 7, and 8, respectively), are used for scientific studies and industrial productions (Figure 2

• ) [31][32][33][34][35]. CDs exhibit the same heights, although the diameters of their cavities differ according to the number of glucose units. As all the hydroxy groups are directly outside the cavity, CDs exhibit hydrophilic and hydrophobic outer and inner structures, respectively, making the CD

• six glucose units exist in the usual CD molecules, causing the necessity of the purification step to isolate only the mono-substituted product from the mixture containing others, such as two- or three-substituted species or the starting material (CD) itself. For example, a typical mono-substituted α

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• with TMS-protected ᴅ-glucosyl iodide, generated in situ by reaction of penta-O-trimethylsilyl-ᴅ-glucose (6b) afforded indigo-N-α-ᴅ-glucoside 7d, albeit, in low yield (Scheme 10) [21]. The reaction of 13 with TMS-protected ᴅ-mannosyl iodide, generated in situ by reaction of penta-O-trimethylsilyl-ᴅ

• pivaloyl-protected N-glycosyl anilines also proved to be unsuccessful, which pointed to steric reasons. Therefore, we studied in our group the use of the less sterically hindered formyl instead of acetyl or pivaloyl protective groups. The reaction of glucose (22a) with aniline afforded anomerically pure N

• isatin-N-glycosides derived from β-ᴅ-galactose, β-ᴅ-glucose, and β-ᴅ-xylose which might be due to their 1,2-trans configuration. An identical relative configuration (1,2-trans; 1,3-cis) is observed for the first three carbon atoms of β-ᴅ-galactose, β-ᴅ-glucose, and β-ᴅ-xylose. In contrast, for β-ᴅ

Deciphering the mechanism of γ-cyclodextrin’s hydrophobic cavity hydration: an integrated experimental and theoretical study

• Stiliyana Pereva,
• Stefan Dobrev,
• Tsveta Sarafska,
• Valya Nikolova,
• Silvia Angelova,
• Tony Spassov and
• Todor Dudev

Beilstein J. Org. Chem. 2024, 20, 2635–2643, doi:10.3762/bjoc.20.221

• characteristic; Introduction Cyclodextrins (CDs), the remarkable macrocyclic molecules with significant impact on our daily life, have completed their 130th anniversary in 2021 [1]. These cavitands are made of 6–9 glucose fragments, linked with 1-4 α-glycosidic bonds. Most common is the β-CD with 7 glucose

• molecule (O2/O3 side of the truncated cone). These hydrogen bonds have been detected experimentally by NMR: it was supposed that the OH-3 group of one glucose monomer is interacting with the OH-2 group of the neighboring glucose unit [21][22]. Experimental evidence for the involvement of primary hydroxy

• and OH-3 of one monomeric glucose unit. Construct е, in which the water molecule binds to OH-2 and OH-3 groups from two adjacent monomers, is not as energetically favorable. As the calculated relative enthalpies of the resulting complexes with water molecules positioned inside the CD cavity (Figure 2

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

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• -pot process can be conducted in various solvents such as in PEG 400 [79], ionic liquids like 1-butyl-3-methylimidazolium hydroxide ((Bim)OH) [80], the nanoionic liquid 1-methylimidazolium trinitrocarbide ([[HMIM]C(NO2)3]) [81], N-methylpyridinium tosylate (NMPYT) [82], or glucose-based strong eutectic

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

• obtain new fluorescent products [39]. Starting from perbenzylated β-C-glucopyranosyl aldehyde 26, 2-aminopyridine (1) and cyclohexyl isocyanide (11), they synthesized C-glucoside 28 (Scheme 11). β-C-Glucopyranosyl aldehyde 26 was obtained from ᴅ-glucose following a procedure already established [40

• (Scheme 13). Glycal aldehydes 32 were synthetized starting from ᴅ-glucose and ᴅ-galactose, following an established procedure [40]. The scope of the reaction was evaluated using differently substituted amidines, and 9 different 2-(β-ᴅ-glycal-1-yl-)-3-N-alkylamino-1-azaindolizines 33 were synthesized in

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

• -directed mutagenesis experiments. Another ι-carrageenase, Car1293, was identified, expressed in E. coli, and characterized from macroalgae-associated Microbulbifer sp. YNDZ01 [89]. β-Glucosidases The β-glucosidases are enzymes that can hydrolyze the β-ᴅ-glycosidic bonds to release glucose at the non

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• (2b) consists of one glucose and one gentiobiose unit, crocin-III (2c) comprises two glucose molecules, crocin-IV (2d) contains only one gentiobiose moiety, and crocin-V (2e) has only one glucose moiety (Figure 1 and Table 1). Pure crocins form reddish-brown acicular crystals with a slight odor. They

• crocins The late steps in crocin biosynthesis are the glycosylation of crocetin (1) by various UGTs [86]. The crocin biosynthetic pathways in G. jasminoides have been characterized in detail, and several GjUGTs were identified. Attributed to different substrate specificities, the glucose or gentiobiose

• the total crocin content [114]. The supply of UDP-glucose is a rate-limiting step in crocin biosynthesis. Glucose is first phosphorylated to generate glucose-6-phosphate by hexokinase and then converted into glucose-1-phosphate by phosphoglucomutase (PGM1). Afterwards, UTP-glucose-1-phosphate

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

• University. To stimulate siderophore production, H002 was grown in modified minimal medium containing casamino acids and glucose as nitrogen and carbon sources, respectively, in the presence of HP-20 resin. Upon cultivation for one week, the non-polar resin was collected and washed thoroughly with water to

• M9 salts (0.7% K2HPO4, 0.2% KH2PO4, 0.01% MgSO4, 0.1% (NH4)2SO4, 0.06% NaCl), 1% glucose, 1% casamino acids, and HP20 resin (Diaion, Mitsubushi Chemical), in forty baffled acrylic flasks. After growth at 30 °C/140 rpm for seven days, the cultures were filtered through cotton to obtain the HP20 resin

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

• for 2 days. Subsequently, they were inoculated into XISR I and XISR III liquid media (total volume 30 L) with a 20% inoculum dose. The cultures were further fermented for 14 days at 28 °C and 200 rpm. Media recipes XISR I medium (yeast extract 4 g/L; malt extract 10 g/L; glucose 4 g/L; MgCl2 1 µM

• ; FeSO4 1 µM; KI 2 g/L, KCl 2 g/L, KBr 2 g/L, NaNO2 2 g/L; H2O2 20 µM; (methyl jasmonate) MeJA 10 µM). XISR III medium (yeast extract 4 g/L; soy flour 10 g/L; glucose 30 g/L; MgCl2 1 µM; FeSO4 1 µM; KI 2 g/L, KCl 2 g/L, KBr 2 g/L, NaNO2 2 g/L; H2O2 20 µM; MeJA 10 µM; 5-azacytidine 6 µM; suberoylanilide

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• aminocyclitol moieties. The biosynthesis of the aminocyclitol has been proposed to proceed through six enzymatic steps from glucose 6-phosphate through myo-inositol to the final methylenedioxy-containing aminocyclitol. Although there is some in vivo evidence for this proposed pathway, biochemical support for

• essential for in vivo antimicrobial activity suggesting a distinct biological function independent of ribosome binding. The hygromycin A biosynthetic gene cluster has been identified and the biosynthesis of the aminocyclitol has been proposed (Figure 1) [8][9]. Starting from glucose-6-phosphate, the pathway

• is hypothesized to proceed through six steps to the final methylenedioxy-containing aminocyclitol. First, glucose-6-phosphate is thought to be converted to myo-inositol by the myo-inositol-1-phosphate synthase Hyg18 and phosphatase Hyg25. Myo-inositol is then proposed to be oxidized by the

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• EzBioCloud [24]. A phylogenetic tree was constructed based on the neighbor-joining method [25] by using MEGAX [26]. Fermentation Saccharopolyspora sp. KR21-0001 was inoculated into 100 mL of seed medium (2.4% soluble starch, 0.1% glucose, 0.3% peptone, 0.3% meat extract, 0.3% yeast extract, and 0.4% CaCO3

Spatial arrangements of cyclodextrin host–guest complexes in solution studied by ¹³C NMR and molecular modelling

• Konstantin Lebedinskiy,
• Ivan Barvík,
• Zdeněk Tošner,
• Ivana Císařová,
• Jindřich Jindřich and
• Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

• complex of 1 with α-CD. Interatomic distances within the host–guest complex were measured using rotating-frame nuclear Overhauser effect spectroscopy (ROESY) measurements. For the complex of 1 with α-CD, the cross-peak in the 2D ROESY spectrum between proton 5 of the glucose moiety of the host α-CD and

• the protons 6 of molecule 1 reveals deep penetration of the guest into the cavity of α-cyclodextrin (Figure 2). All protons of 1 show ROESY cross-peaks with proton 3 of the glucose unit (see page S73 in Supporting Information File 1). For complexes of ligands with α-CD, we always performed a series of

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• inoculated into 10 mL of Tryptone Soya Broth (TSB) medium with kanamycin (50 mg/L) and incubated with shaking (300 rpm) at 30 °C for 2 days. One milliliter of this preculture medium was inoculated into 100 mL of Waksman medium (5 g/L BactoTM peptone, 5 g/L BactoTM yeast extract, 20 g/L glucose, 5 g/L meat

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• 13.96 and 22.16 min were coincident with those of the ᴅ-glucose and ʟ-rhamnose derivatives, respectively. Although the peak at 20.83 min was assumed to be attributable to apiofuranose, we were unable to obtain any standard for apiofuranose. In the reported monosaccharide identification method, the

• retention times of the ᴅ-glucose, ʟ-rhamnose, ᴅ-apiose, and ʟ-apiose derivatives were 17.48, 29.47, 28.57, and 15.69 min, respectively, with the ᴅ-apiose derivative having a longer retention time than the ʟ-apiose derivative [16]. Therefore, considering the retention times of the ᴅ-glucose (13.96 min) and ʟ

• identification, which revealed peaks at retention times of 13.97 (ᴅ-glucose), 20.84 (ᴅ-apiose), and 22.17 (ʟ-rhamnose) min. Hence, 2 was identified as breynogenin-β-S-oxide 3-O-β-ᴅ-apiofuranosyl-(1→2)-[α-ʟ-rhamnopyranosyl-(1→3)]-β-ᴅ-glucoptranosyl-(1→2)-β-ᴅ-glucopyranoside. Furthermore, we investigated the

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

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

• was shown to be a key player in lanostane triterpenoid cytotoxicity; increased activity was demonstrated either by its esterification with glucose or by its reduction into a hydroxymethylene group unlike its presence as a free carboxylic acid moiety [23]. Thus, our findings provide further insights

• was weighed out into 10 × 500 mL Erlenmeyer flasks, each containing 90 mL of deionized H2O and autoclaved. In addition, 20 × 200 mL Erlenmeyer flasks containing cotton seed flour (Q6/2) liquid-state fermentation media were prepared as follows: media components (ᴅ-glucose 2.5 g/L, glycerol 10 g/L

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

• acids, 0.5 g/L glucose, 0.5 g/L soluble starch, 0.3 g/L KH2PO4, 0.05 g/L MgSO4 × 7 H2O. The pH of the medium was adjusted to pH 7.2. The cultivation was conducted on a rotary shaker at 130 rpm and 30 °C for one week. Afterwards adsorber resin (XAD-7, 20 g/L) was added to the culture broth to bind the

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

• % CO2 atmosphere using high-glucose DMEM (GIBCO, USA) containing 10% fetal bovine serum (FBS, GIBCO, USA), 100 U/mL penicillin, 10 μg/mL streptomycin, and 10 μg/mL puromycin. Cells were seeded at a density of 5000 cells/well in 96-well plates under the same incubation conditions. Following overnight

• cell line) cells were incubated in high-glucose DMEM (GIBCO, USA) containing 10% fetal bovine serum (FBS, GIBCO, USA), 100 U/mL penicillin, and 100 μg/mL streptomycin. Cells were maintained in an atmosphere of 5% CO2 at 37 °C and subsequently plated in 96-well plates at a concentration of 2 × 104 cells