Recent advances in total synthesis of illisimonin A

• Juan Huang and
• Ming Yang

Beilstein J. Org. Chem. 2025, 21, 2571–2583, doi:10.3762/bjoc.21.199

• embellished by additional bridging via a γ-lactone and a γ-lactol ring, resulting in a caged pentacyclic scaffold with a 5/5/5/5/5 ring arrangement. The compound demonstrates neuroprotective activity by mitigating oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells. Since its isolation in 2017

• neuroprotective effects against oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells, suggesting its potential as a lead compound for the treatment of neurodegenerative diseases. The possible biosynthetic pathway of illisimonin A was also proposed by Yu and co-workers, as illustrated in Scheme 1. The

Ex-situ generation of gaseous nitriles in two-chamber glassware for facile haloacetimidate synthesis

• Nikolai B. Akselvoll,
• Jonas T. Larsen and
• Christian M. Pedersen

Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188

• transformation of the peracetylated glucose hemiacetal 2 in the other chamber (B), giving 73% isolated yield of the corresponding acetimidate 6 (Figure 2). Similarly, the chlorodifluoroacetimidate 7 was synthesized in 79% yield. From these reactions it is clear that the less reactive (disarmed) peracetylated

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• reported a stereospecific reduction of an acyloin ring controlled by the chirality of a glucose fragment at position C5, and suggested a possible mechanism for hydrogen migration during the conversion of C5 (sp2) to C5 (sp3). The key 3,4,6-trihydroxycyclohexadienone 76 was obtained by a sequence of Friedel

• with 52% yield (Scheme 14). The authors [47] provided convincing evidence that the acyloin ring contraction is stereospecific, by replacing the benzil ᴅ-glucose in compound 76 at the C5 atom with an achiral prenyl group. In [49], Zhang and co-workers carried out the first enantioselective synthesis of

Halogenated butyrolactones from the biomass-derived synthon levoglucosenone

• Johannes Puschnig,
• Martyn Jevric and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2025, 21, 2297–2301, doi:10.3762/bjoc.21.175

• been reported in a 12-step procedure starting with glucose in an overall yield of 2% [24]. Enol esters [25], enolates [26], enamines [27][28], and silyl enol ethers [29], some of which can be derived from LGO, have been used in electrophilic fluorination and trifluoromethylation strategies. It was

C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

• hemicellulose, dehydration to furfural, hydrogenation into furfuryl alcohol and final hydrolysis to levulinic acid (Scheme 70, route a). The second route is the acid-catalyzed multistep conversion of polysaccharides into C6 monosaccharides (glucose and fructose), followed by dehydration to 5-HMF, and then

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

• that of brain tissue. The hydrogel’s hypoxia-responsive properties were validated through three different systems: sodium dithionite (SDT), rat liver microsomes, and the oxygen-glucose deprivation (OGD) model. Under hypoxic conditions, the hydrogel achieved targeted release of cyanine 5-dimethyl (CY5

• -DM) or fingolimod (FTY720) in vitro. Upon local administration, the hypoxia-responsive self-assembling peptide hydrogel resulted in improved motor function and reduced inflammation in vivo. Recently, Geng and colleagues created additional binding sites by modifying the upper rim of CA4 with glucose

• side effects associated with intravenous thrombolysis using recombinant tissue-type plasminogen activator (rtPA) for treating ischemic stroke. The interaction between GluAC4A and Lip results in a significant improvement in Lip’s solubility. The glucose modification on the upper rim of GluAC4A serves

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

• tetrabenzylated glucose lactol acceptor 2, resulting in the formation of the β,α-1,1-linked diglucoside 3 (Scheme 1) [49]. The application of a the 2,3,4,6-tetra-O-benzyl trichloroacetimidate donor 4 resulted in the same disaccharide product 3, albeit as part of a mixture with other diastereomers [51]. The

• and K. pneumoniae [74][75]. The application of variably protected 3-azido-3-deoxy-glucose-derived donor 72 and lactol acceptor 73, both allegedly armed due to the presence of multiple electron-donating bulky substituents, did not lead to product formation in the TMSOTf-promoted glycosylation reaction

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

• human system. In this study, we isolated two previously undescribed N-salicyl-amino acids as natural products (1 and 2) and other two new derivatives (3 and 4) from the organic extract of a culture broth in a modified starch–glucose–glycerol (SGG) medium of Pseudomonas sp. UIAU-6B. The structure of the

• sample collected off the heavy metal-contaminated Oyun River in Nigeria. The isolation and identification of the bacterial strain UIAU-6B has been previously reported [15]. Small-scale culture Pure colonies of the Pseudomonas sp. UIAU-6B were inoculated into 100 mL of SGG (10 g of glucose, 10 g of

Oxetanes: formation, reactivity and total syntheses of natural products

• Peter Gabko,
• Martin Kalník and
• Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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

• and mercury. For now, let us look at what cyclodextrins are and which properties make them so special and versatile for use in a variety of industrial processes. Originating from starch – a helicoidally shaped glucose chain – cyclodextrins are small fragments that are sectioned off and linked back

• together to form cyclic oligosaccharides. The naturally occurring cyclodextrins, also named native cyclodextrins, have typically six (α-CD), seven (β-CD) or eight (γ-CD) ᴅ-glucose units [26][27]. Their monomers are all linked by α-1,4 glycosidic bonds, which results in a molecular geometry with a shape

• that resembles a truncated cone. Secondary hydroxy groups of the glucose residues are directed towards the wider rim of the cone, and primary hydroxy groups, bound to C6, face the narrower rim, which overall conveys them with good aqueous solubility. The inner cavity of the cone is, in turn, lined with

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

• (Scheme 21C) [55]. Kawabata and co-workers (2020) prepared the β-glycoside 66 from α-ᴅ-glucose and cinnamic acid (7) in good yield through the Mitsunobu reaction (Scheme 22) [56]. The 13C kinetic isotope effect experiment (KIE = 1.028) showed that the glycosylation proceeded via SN2 substitution (67). Sun

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

• Valentina Benazzi,
• Arianna Bini,
• Ilaria Bertuol,
• Mariangela Novello,
• Federica Baldi,
• Matteo Hoch,
• Alvise Perosa and
• Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

• different organic sources as photoreductants. Such carbon nanomaterials were synthesized by two different approaches, either hydrothermal or pyrolytic, from citric acid and glucose as the starting organic substrates. On the other hand, carbon dots deriving from fishery waste (bass scales) and fruit

• efficiency of the resulting CDs. In this context, citric acid-derived materials (both graphitic and amorphous) were found as the most promising materials, while less satisfactory results have been observed when using CDs derived from glucose and biowastes. Keywords: agricultural waste; carbon dots (CDs

• have been considered as a promising source of aryl radicals and employed in organic synthesis [20][21][22][23][26][27][28][29][30][31][32]. This investigation aims to compare the performance of CDs prepared from several carbon precursors including citric acid, glucose, and organic waste materials via

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