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

• states of the bis-azobenzene glycocluster 6βGlc3αMan 1 representing different relative Man/Glc orientations. In order to put the biological properties of the previously described photoswitchable heterobivalent cluster glycoside 6βGlc3αMan 1 [24] into perspective, several relevant analogs were synthesized

• , namely the homobivalent cluster glycoside 6αMan3αMan 2 and the glycoazobenzene portions contained in 1 and 2, i.e., the glycoazobenzene-functionalized mannosides 6βGlc 3, 6αMan 4, and 3αMan 5 (Figure 1). In this account, the photochromic properties of the glycoconjugates 1–5 were compared and their

Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

• that lies outside the sugar ring, is the C-1–O anomeric bond in glycosides (highlighted in 74, Figure 10). This anomeric bond serves as a linker between the sugar and the rest of the glycoside; rotation about this bond can dramatically change the overall shape of the molecule, which in turn can affect

• ). Carbasugars are of broad interest because they can be used to create non-hydrolysable glycoside mimics; however, they are poor mimics of genuine glycosides in terms of the rotational profile about the anomeric bond. In true glycosides (e.g., 74, Figure 10), the anomeric bond typically does not rotate freely

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

• Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

• typically not possible for imine [314] or metal-coordination cages [156][202][365]. Further, the robust amide cages could withstand harsh conditions such as ester hydrolysis, allowing access to the key acid-functionalized cages [38] that mimic aspartyl proteases and glycoside hydrolases. Otte has employed

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• glycosylation. Conventional glycosylation involves the ‘nucleophilic substitution’ of the leaving group at the sp3 anomeric centre of the donor moiety with a suitable carbohydrate or non-carbohydrate-based aglycon with the help of an electrophilic promoter to form the equatorial glycoside 7 or the axial

• glycoside 8 (Scheme 1). Glycosylation is considered as the most crucial step in any oligosaccharide synthesis, although it may be argued that, building block preparations or final deprotection steps remain equally demanding. The main challenge of glycosylation lies in the structural complexity of the

• pathway through an associative transition state to form the equatorial glycoside, 7. Surprisingly, recent evidences show that typical homogeneous glycosylation reactions in organic solution shift more towards the SN2 end of the mechanistic spectrum [32][33][34], with some exceptions [35]. The kinetic

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

• material in Europe (Scheme 1). It is obtained by extraction and isolation of the colorless indole-O-glycoside indicane which is then hydrolyzed to give indoxyl. The latter undergoes oxidative dimerization to provide indigo. In the 19th century, syntheses of indigo were developed which made the pigment

• (Scheme 4) [20]. The reaction of 1b with 3,4,6-tri-O-acetyl-2-O-benzoyl-α-ᴅ-glucosyl trichloroacetimidate (6a) afforded indigo-N-glycoside 7a. The benzoyl group located at OH-2 seemed to be unreactive enough to avoid formation of orthoester-like amide acetals during the N-glycosylation with 1b. Oxidative

• -glycoside 11a (Scheme 7) [20]. Debenzylation gave product 11b which was transformed to akashin A (11c) by reduction of the azide to the amine in the presence of propane-1,3-dithiol and subsequent debenzoylation. Akashin A was transformed to akashins B and C by acetylation and reaction with diacetyl

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

• are glycoside hydrolases (GHs) that degrade agarose to smaller oligosaccharides [102]. Marine bacteria of diverse genera produce agarases [103][104][105]. Based on the reactions that they catalyze, bacterial agarases are grouped as α- and β-agarases wherein they hydrolyze α-1,3 linkages and β-1,4

• linkages in agarose, respectively (Figure 2). However, based on sequence similarity, agarases are alternatively classified into different families of glycoside hydrolases (GHs): GH-96 and GH-117 for α-agarases, and GH-16, GH-50, GH-86, and GH-118 for β-agarases [106]. All agarases characterized from

• macroalgae-derived Microbulbifer sp. YNDZ01 and expressed in E coli [88]. The recombinant enzyme Lip4346 showed high stability at high temperatures and in alkaline conditions, and tolerance to organic solvents. α-Amylases are glycoside hydrolases that catalyze the hydrolysis of internal α-1,4-O-glycosidic

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• -isomer is twice better than for its Z-counterpart for the S-linked compound 3 and three times better for the O-glycoside 1. Even though the other compounds do not exhibit significant variations of affinities between E- and Z-isomers, a closer look at the thermodynamic values indicates that the mechanisms

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• yield (92%) and formed the diol 77, after the removal of the Boc-protecting group, where the prochiral hydroxymethyl groups ultimately paved the way towards the natural products (Scheme 22). Bernhardson and coworkers developed a simple scalable route towards ertugliflozin (80), a C-glycoside containing

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

• pharmaceutical industries [5]. They exhibit a broad spectrum of pharmacological activity, including antitumor [6], anti-inflammatory [7], hepatoprotective [8], nephroprotective [9], antidepressant [10], antioxidant [11], and antidiabetic [12] properties. The Saffron Multi-glycoside Tablet (Xihonghua Zonggan Pian

Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

• Kairi Umeda,
• Naoaki Kurisawa,
• Ghulam Jeelani,
• Tomoyoshi Nozaki,
• Kiyotake Suenaga and
• Arihiro Iwasaki

Beilstein J. Org. Chem. 2024, 20, 645–652, doi:10.3762/bjoc.20.57

• polycavernosides. Keywords: macrolide glycoside; marine cyanobacterium; marine natural products; polycavernosides; terminal alkyne; Introduction In 1991, an outbreak of food poisoning caused by a species of red algae known as ‘Polycavernosa tsudai’ occurred in Guam, which resulted in killing of three people. Two

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

• inducing cytotoxicity. In addition, another study demonstrated that a lanostanoid glycoside derivative with a glucosyl ester at the C-21 carboxylic acid group was active in a cytotoxic activity assay, whereas the galactosyl ester counterpart was inactive [36]. Similarly, the carboxylic acid group at C-21

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• :1). Additional transformation of compound 230 following an A–AB–ABC synthetic strategy resulted in the desired complex tricyclic skeleton opening the door for the total synthesis of 12-epi-JBIR-23/24 (Scheme 61). The sulfated β-glycoside peyssonnoside A was isolated only recently from the red algae

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• [64][65][66]. The goal of this study was the synthesis of β-CD/hazelnut (Corylus avellana L.) oil/flavonoid glycoside or flavonolignan ternary complexes (Figure 1) and the discrimination of these complexes by FTIR–PCA. These innovative ternary complexes were synthesized for the first time and can

• kneading method as the most appropriate one for obtaining β-CD/hazelnut (Corylus avellana L.) oil/flavonoid glycoside or flavonolignan ternary complexes. Kneading allows for higher recovery yields of complexes in comparison with the co-crystallization method because only small amounts of solvent are needed

• discrimination of such ternary complexes on the basis of FTIR. The evaluation of the encapsulation competitiveness of such multicomponent mixtures is very challenging (highly hydrophobic FA triglycerides, mono- and diglycerides, free FAs, as well as more hydrophilic flavonoid glycoside, namely hesperidin

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• molecules into the cavity of the glycoside micelles should be taken into account. Our main goal in this part of the study is to guarantee that the prepared foams remain stable at least until the crosslinking reaction takes place. Once the six experimental synthetic paths were set (see Experimental section

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• typically found as a terminal unit of surface glycoconjugates and is crucial to various cellular recognition events in both physiological and pathological processes [1]. This distinctive negatively charged monosaccharide is the natural substrate for sialidases, which belong to different glycoside hydrolase

• anomeric configuration of 1 was based on the chemical shift of H3eq, which is located in lower magnetic field (over 2.5 ppm) when compared to a β-glycoside (under 2.5 ppm) [27]. Additionally, the anomeric configuration can be determined through the coupling pattern of C-1 in a selective proton decoupled

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• 106.8, 103.0, 79.0, 78.9, 77.9, 75.4, 74.8, 71.4, 71.5), as well as two oxygenated methylenes resonated at δC 70.6, and 67.7, respectively. The aforementioned information suggested that compound 1 is likely a bis-coumarin glycoside [9]. The substructures A and B (Figure 2 and Figure 3) were elucidated

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• Streptomyces, are especially noted, accounting for more than 800 metabolites of actinomycetes origin [11], which include the antiinfective aminoglycoside gentamicin [13], antidiabetic glycoside acarbose [14], glycopeptide antibiotic teicoplanin [15], enediyne antitumor component of drug-antibody conjugate

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• was then deprotected and N-acetylated to finally afford the desired trisaccharide repeating unit as its α-p-methoxyphenyl glycoside. Keywords: capsular polysaccharide; carbohydrate vaccines; O-antigen; oligosaccharide synthesis; one-pot synthesis; Introduction O-antigens or O-specific

• -methoxyphenyl glycoside form 1 was synthesized through a linear [1 + (1 + 1 = 2)] strategy. The target trisaccharide was synthesized as its p-methoxyphenyl glycoside that offered the unaltered stereochemistry of the sugar at the reducing end to mimic the glycosidic linkage of the natural polysaccharide. The

• stereoselective glycosylations. The work provides an access to the trisaccharide repeating unit of the O-polysaccharide of Providencia stuartii O49 with the stereospecific α-p-methoxyphenyl glycoside. Structure of the repeating unit of the lipopolysaccharide of Providencia stuartii O49 serotype. Retrosynthetic

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• , Figure 1B) form via the polymerization of multiple glycoside units. The ports on both sides of these compounds are surrounded by carbonyl oxygen atoms, which form a hydrophobic cavity and two hydrophilic ports [20]. The outer surface of the cucurbit[n]uril is composed of a large number of nitrogen atoms

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• stereoselectivity during β-selective glycosidic bond formation. The general pathway for glycosidic bond formation (Figure 4) shows that the glycoside donor moiety has to be activated using an appropriate activator to form an oxonium ion. The attack of a nucleobase (glycosyl acceptor) may occur on either side of the

• oxonium ion, which can result in two anomers, i.e., an α- and a β-anomer. The factors affecting such stereocontrolled glycoside bond formations are also discussed in this review. The preparation of the racemate 1c was reported by Belleau et al. in 1989 (Scheme 26) [38]. The method involved the coupling of

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• of Biopharmaceutical Convergence, Sungkyunkwan University, Suwon 16419, Republic of Korea 10.3762/bjoc.17.151 Abstract Three new neolignan glycosides (1–3), a new phenolic glycoside (15), and a new cyanoglycoside (16) were isolated and characterized from the twigs of Aleurites fordii together with

• fordii; antineuroinflammation; Euphorbiaceae; neolignan glycoside; neuroprotective activity; phenolic compound; Introduction Aleurites fordii Hemsl. (= Vernicia fordii Hemsl., Euphorbiaceae), known as tung oil tree, is widely distributed throughout Northeast Asia [1]. The fruits, leaves, and roots of

• (1–3), a new phenolic glycoside (15), a new cyanoglucoside (16), and 14 known compounds (4–14 and 17–19) (Figure 1). Compound 1 was obtained as a colorless gum. The molecular formula was determined to be C25H32O11 from the [M + Na]+ molecular ion peak in the positive mode HRFABMS. The 1H NMR data

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• digestion. This compound was then chemically transformed to the corresponding glycosyl donors (4-methoxyphenyl- or fluoro-glycoside) to chemoenzymatically produce complex XGs. Compounds with different substitution patterns were obtained using a glycosynthase from Humicola insolens [105][106]. This approach

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• hydroquinolinone, chromene, piperidine, peptide, lipid, and glycoside moieties (Scheme 2). Bojanowski and co-workers developed a methodology to synthetize 3,4-dihydrocoumarins 10 through a decarboxylative and dearomatizative cascade reaction [33]. This reaction was carried out using coumarin-3-carboxylic acids 8

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126