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

• , the pellet was resuspended in 40 mL of sucrose solution (25% sucrose, 50 mM Tris pH 8) using continuous stirring. Then, 10 mg of lysozyme (Bio Basic) was added and stirred at room temperature for 10 min, followed by the addition of 80 mL deoxycholate solution (1% deoxycholate, 1% Triton X-100, 100 mM

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• Ishige sinicola [22]. The (7Z,10Z)-hexadecadienoyl group has been found in galactoglycerolipids from Chlorella [23][24][25], kale (Brassica oleracea) [26], Daphnia [27], and meadow buttercup (Ranunculus acris, family Ranunculaceae) [28], and as a sucrose ester from rough horsetail (Equisetum hiemale

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• supernatant was recovered and stirred for at least 3 h. Then the sample was layered on a 10% sucrose cushion and ultracentrifuged for 2 hours at 30,000 rpm using an SW-32Ti rotor (Beckman Coulter, USA). Later, the supernatant was discarded and the pellets were resuspended with a virus suspension buffer (50 mM

• sodium acetate, 8 mM magnesium acetate, pH 4.5). The solution was ultracentrifuged through a sucrose gradient at 30,000 rpm for 2 hours, at 4 °C. The virus was recovered from the blue band, and the sucrose was removed by ultracentrifugation. The pellets were resuspended in virus suspension buffer (50 mM

Incorporation of a metal-mediated base pair into an ATP aptamer – using silver(I) ions to modulate aptamer function

• Marius H. Heddinga and
• Jens Müller

Beilstein J. Org. Chem. 2020, 16, 2870–2879, doi:10.3762/bjoc.16.236

• ), 8% sucrose), and desalted using NAP 10 columns. MALDI–TOF spectrometry was used to characterize the oligonucleotides either in a 3-hydroxypicolinic acid (3-HPA)/ammonium acetate matrix or in a 3-HPA in TA50 solvent matrix (50:50, v/v acetonitrile/0.1% TFA in water) containing 10 mg/mL diammonium

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• dehydration of ᴅ-sorbitol using a strong acid catalyst [10][11]. ᴅ-Sorbitol is produced from the hydrogenation of glucose obtained mostly from the hydrolysis of starch, but also from sucrose or cellulose. Consequently, the cellulose valorization can be realized from the one-pot conversion of cellulose to

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• to the precursor solution consisting of sucrose as carbon source and NaCl or NaNO3 as inorganic salt. The pyrolysis of the precursor solution leads to dehydration of carbon as well as iron salt conversion to crystalline or non-crystalline iron species depending on the production conditions. The

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• KCl, 1.25 NaH2PO4, 7 MgCl2, 0.5 CaCl2, 26 NaHCO3, 10 glucose, 100 sucrose, 3 sodium pyruvate, 1.3 sodium ascorbate equilibrated with 95% O2/5% CO2 (pH 7.3–7.4). The brain slices were then incubated for 15 min at 33 °C in artificial cerebrospinal fluid (ACSF, mM: 125 NaCl, 2.5 KCl, 1.25 NaH2PO4, 1

New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita

• Frank Surup,
• Florian Hennicke,
• Nadine Sella,
• Maria Stroot,
• Steffen Bernecker,
• Sebastian Pfütze,
• Marc Stadler and
• Martin Rühl

Beilstein J. Org. Chem. 2019, 15, 1000–1007, doi:10.3762/bjoc.15.98

• ) 5.00 g/L, D(+)-sucrose (Carl Roth GmbH & Co, Karlsruhe, Germany) 4.00 g/L, D-mannitol (AppliChem GmbH, ITW Company, Darmstadt, Germany) 4.00 g/L, D-glucose monohydrate (Cargill Holding Germany GmbH, Krefeld, Germany) 1.50 g/L, CaCO3 (Carl Roth GmbH & Co KG, Karlsruhe, Germany) 1.50 g/L, lactalbumin

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• evaporator. The resulting thin lipid film was further dried for 180 minutes at 1 mbar/25 °C, and then hydrated for 16 hours – without shaking – with the aqueous buffer, termed “I-solution” (composed of 200 mM sucrose in 50 mM of PBS buffer, pH 7.4) to obtain an overall 1–2 mM lipid concentration. The

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• enzymatic synthesis of NR+ from α-D-ribose-1-phosphate and Nam by catalysis with purine nucleoside phosphorylase and sucrose phosphorylase is described in a US patent application by Velasquez et al. [46]. In the NMR experiments, the authors demonstrated the preparation of NR+ but did not isolate pure NR+. 3

First synthesis of cryptands with sucrose scaffold

• Patrycja Sokołowska,
• Michał Kowalski and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2019, 15, 210–217, doi:10.3762/bjoc.15.20

• Patrycja Sokolowska Michal Kowalski Slawomir Jarosz Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland 10.3762/bjoc.15.20 Abstract Cryptands with sucrose scaffold, an unknown class of such derivatives, were prepared from the readily available 2,3,3

• ’,4,4’-penta-O-benzylsucrose and 1’,2,3,3’,4,4’-hexa-O-benzylsucrose. Keywords: cryptands; macrocyclization; sucrose; Introduction The design and synthesis of macrocyclic receptors is one of the main challenges of supramolecular chemistry [1][2]. These artificial systems exhibit interesting properties

• structure. Up to date, only monosaccharides have been intensively used as chiral building blocks in the synthesis of such macrocycles. Less attention, however, has been paid to macrocycles with disaccharides (or oligosaccharides) being a part of the ring [6][7][8]. We have proposed to use sucrose (1) as a

Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

• Karolina Tiara,
• Mykhaylo A. Potopnyk and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2018, 14, 634–641, doi:10.3762/bjoc.14.50

• -O-benzylsucrose with different unsaturated monosaccharide units is presented. Such a highly functionalized intermediate was cyclized under RCM conditions to afford a macrocyclic derivative containing a 31-membered ring in 26% yield. Keywords: chiral macrocycles; ring-closing metathesis; sucrose

• [13], etc. are usually applied as building blocks for construction of such type of compounds. We are engaged in the synthesis of such macrocyclic derivatives containing the most common natural disaccharide, sucrose [14][15]. Several different classes of macrocyclic derivatives, including: crown [16

• ] and aza-crown [17][18] derivatives, macrocyclic dilactams [19][20], and ureas [21], were prepared in our laboratory. Sucrose was also used by other groups as a precursor for the preparation of biodegradable polymers [22][23][24] and polymeric nanoparticles [25]. On the other hand, sucrose derivatives

An efficient synthesis of a C₁₂-higher sugar aminoalditol

• Łukasz Szyszka,
• Anna Osuch-Kwiatkowska,
• Mykhaylo A. Potopnyk and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2017, 13, 2146–2152, doi:10.3762/bjoc.13.213

• building blocks. The synthesis was realized by a regioselective introduction of the azide group and subsequent protection–deprotection transformations. The chemical reactivity of the aminoalditol was tested in the reductive amination reaction with a selectively protected sucrose monoaldehyde. Keywords

• : higher carbon sugars; reductive amination; sucrose; Introduction Carbohydrates, because of their availability in a variety of optical pure forms, are particularly useful in planning and executing the synthesis of chiral macrocyclic compounds [1][2][3][4][5]. In this context, polyhydroxylated derivatives

•  1). This compound can be modified selectively at either terminal position: C1 (OH group) or C12 (NH2 group). Since we are engaged in the preparation of complex derivatives of sucrose (Figure 2) [9][10][11][12][13][14][15][16] we decided to prepare a sucrose derivative with this aminoalditol pendant

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

• remarkably simple protocol that allows for a C3′-regioselective glycosylation of unprotected sucrose under aqueous conditions has been described by Schepartz, Miller and colleagues [57]. They took advantage of the fact that most glycosyl transferase enzymes operate in a divalent metal cation-dependent

• -enzymatic glycosylation procedure. After extensive optimization, the authors obtained the regioselective C3′-glycosylated sucrose analog in very good yield with complete inversion of stereochemistry at the anomeric position (Scheme 16) by using Ca(OTf)2 and NMe3 (aq). Two of the most remarkable substrates

• sequentially deoxygenated sucrose derivatives and quantified H-to-D isotope exchange effects (from the deuterated solvent) using 1H NMR techniques. They concluded that it is the complex hydrogen-bonding network present in sucrose that played the key role in determining the reactivity and selectivity of the

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• 1930, the first crystal structures of organic compounds to be investigated were carbohydrates of low molecular weight. Over the following years, only eight additional crystal structures were reported. The determination of the three dimensional structure of the dehydrated form of sucrose, in 1947, was

• few thousand entries for carbohydrate crystal structures, among which a limited number of molecules are relevant to glycobiology. With the exception of sucrose and cyclic compounds, such as cyclodextrins or cyclo-amyloses, carbohydrates are reluctant to crystallize in form and size suitable for X-ray

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• co-workers produced a nanogel injectable in humans to detect cancer cells. The nanogel was composed by sucrose acetate isobutyltyrate (SAIB) and poly(N-isopropylacrylamide) (PNIPAM)-coated AuNPs, compatible with SAIB matrix. The nanogel had good opacity for 2D X-ray visualization and was tested in

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• least 1 h for evaporation of remaining traces of the solvent. Lipid-coated slides were assembled using a spacer of Parafilm (Pechiney Plastic Packaging, Chicago, IL, USA) for insulation. The electroswelling chamber was filled with 1 mL sucrose buffer (250 mM sucrose, 15 mM NaN3, osmolarity of 280 mOsm

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• of novel FCDs with improved properties. For example, simple monosaccharides such as glucose, glucosamine, mannose, fructose and their derivatives and common disaccharides, e.g., sucrose, lactose, and maltose have been employed to prepare fluorescent carbon dots (FCDs) using different methodologies

• materials were obtained when the team used sucrose or starch as starting carbohydrate materials. In addition to microwave and acid reflux-mediated glucose dehydration reactions, the group of Wang developed an alternative protocol that combined glucose with monopotassium phosphate (KH2PO4) in a Teflon-lined

• ]. It was found that irradiation times of 14 min could be employed to afford CDs from glycerol, glycol, glucose or sucrose. The source of the inorganic ion was important too, as increasing the valency of either the anion or cation would lead to a greater ability to dehydrate the carbon precursor. An

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• times sweeter than sucrose. Thaumatin has been shown to bind to G-protein-coupled receptors (GPCRs) which are transmembrane proteins, responsible for signal transduction. Therefore, the interaction of CDs with thaumatin could be used to modify the interaction of thaumatin with GPCRs and to modify its

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• remarkable example is the recently patented synthesis of sucrose-6-ester – a food sweetener – carried out over a mixture of sulfated oxides of various metals [8]. In addition, acidic ion exchange resins are worth mentioning in this context. Van de Steene et al. have proved the performance of such systems in

Stereoselective synthesis of hernandulcin, peroxylippidulcine A, lippidulcines A, B and C and taste evaluation

• Marco G. Rigamonti and
• Francesco G. Gatti

Beilstein J. Org. Chem. 2015, 11, 2117–2124, doi:10.3762/bjoc.11.228

• ; lippidulcines; Saegusa–Larock; Introduction It is a matter of fact that a large consumption of sucrose is strongly associated to a considerable number of undesirable health effects, among which cardiovascular diseases and dental caries are the most relevant. Moreover, the increasing number, especially in the

• 1000 times as sweet as sucrose. More recently other derivatives of 1 have been discovered, i.e., the peroxylippidulcines 2a–c and the lippidulcines 3a–c (Figure 1) [7][8]. However, these sesquiterpenes have been isolated in a so small amount that it has not been possible to assess their taste. In

Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

• César A. Estévez,
• José Ramón Isasi,
• Eneko Larrañeta and
• Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

• : controlled release; cyclodextrins; lactase; polypseudorotaxane; supramolecular gel; Introduction In the Western diet, carbohydrates contribute about 50% of calories, distributed in the following ratio: starch (50%), sucrose (30%), lactose (6%), maltose (1–2%), and others (12%: trehalose, glucose, fructose

• , sorbitol, cellulose, hemicellulose and pectin). Lactose, sucrose and maltose constitute a significant proportion, especially in infants, whose sole or main source of food is milk [1]. Disaccharides, such as lactose, must be hydrolyzed in order to be absorbed by the human body. For absorption to occur

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• Ginkgo biloba collected in the campus of Nanjing University (Nanjing, P. R. China), in October 2008 [7]. The strain was cultured on MEA (consisting of 20 g/L malt extract, 20 g/L sucrose, 1 g/L peptone, 20 g/L agar and deionized water) at 28 °C for 5 days. Agar plugs were used to inoculate in 1000 mL

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

• Melanie Rauschenberg,
• Eva-Corrina Fritz,
• Christian Schulz,
• Tobias Kaufmann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

• any interaction with HisHis should not lead to a decrease in the fluorescence of FITC-HisHis on the microarray and this is indeed observed for methyl α-D-mannoside, methyl β-D-glucoside, methyl β-D-fucoside, trehalose, sucrose as well as N-acetylglucosamine (see Figure 7G–L). These experiments

• incubation with FITC-HisHis and methyl β-D-galactoside; (G) washing of (A) with 500 mM methyl α-D-mannoside; (H) washing of (A) with 500 mM methyl β-D-glucoside; (I) washing of (A) with 500 mM methyl β-D-fucoside; (J) washing of (A) with 500 mM trehalose; (K) washing of (A) with 500 mM sucrose; (L) washing

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

• Zbigniew Pakulski,
• Norbert Gajda,
• Magdalena Jawiczuk,
• Jadwiga Frelek,
• Piotr Cmoch and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

• Zbigniew Pakulski Norbert Gajda Magdalena Jawiczuk Jadwiga Frelek Piotr Cmoch Slawomir Jarosz Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland 10.3762/bjoc.10.124 Abstract The reaction of appropriately functionalized sucrose phosphonate with

• sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was

• synthesis; sucrose; Introduction Molecular recognition is one of the most important phenomena in stereoselective processes. Chiral crown ethers (or analogs) are particularly useful in enantioselective reactions [1][2] as well as differentiation of chiral guests [3][4]. From all of the chiral platforms