Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• . As the prepared porous polymer SugPOP-1 is based on hemiacetal glucose, Ag nanoparticles (AgNPs) can be successfully incorporated into the polymer by an in situ chemical reduction of freshly prepared Tollens’ reagent. The obtained AgNPs/SugPOP-1 composite demonstrates good catalytic activity in the

• porous polymer SugPOP-1 is based on hemiacetal glucose, it was further postfunctionalized to embed the AgNPs into the material using an in situ chemical reduction of the freshly prepared Tollens’ reagent. The related catalytic reduction by the AgNPs/SugPOP-1 composite was also explored at room

• porous polymers containing a hemiacetal glucose motif (SugPOP-1), AgNPs were smoothly embedded into the material by chemical reduction of freshly prepared Tollens’ reagent, allowing in situ formation of AgNPs in the polymer matrix. With a high porosity and micro-/mesoporous features, the AgNP-loaded

Kinetic analysis of mechanoradical formation during the mechanolysis of dextran and glycogen

• Naoki Doi,
• Yasushi Sasai,
• Yukinori Yamauchi,
• Tetsuo Adachi,
• Masayuki Kuzuya and
• Shin-ichi Kondo

Beilstein J. Org. Chem. 2017, 13, 1174–1183, doi:10.3762/bjoc.13.116

• , Japan 10.3762/bjoc.13.116 Abstract A detailed electron spin resonance (ESR) analysis of mechanically induced free radicals (mechanoradicals) formation of glucose-based polysaccharides, dextran (Dx) and glycogen (Gly) was performed in comparison with amylose mechanoradicals. The ESR spectra of the

• initiate the polymerization is frequently used to synthesize such a graft polymer [7]. Dextran (Dx), a biodegradable polysaccharide, has been utilized as a graft copolymer backbone. The glycosidic linkages between the α-glucose units of Dx synthesized from Leuconostoc mesenteroides are composed of

• mechanoradical formation from Dx and Gly at room temperature in detail. To obtain fundamental insights into the mechanolysis of Dx and Gly, we conducted detailed ESR spectra analyses of the Dx and Gly mechanoradicals in comparison with those of amylose. Because amylose is an α-glucose-based polysaccharide and

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

• considered a significant contribution to the field. A major breakthrough occurred in 1951, when Bijvoet confirmed, without ambiguity, the D-configuration of glucose, which had been assigned from indirect reasoning by Emil Fischer in 1891 [10]. At the present time, the Cambridge Structural Database contains a

• transport proteins GLUTs are responsible for the diffusion of glucose, galactose, fructose, urate, myoinositol, and dehydroascorbic acid. SGLTs are sodium-glucose symporters that couple the transport of glucose to sodium ions. SWEETs have been characterized the most recently. Major carbohydrate transporters

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

• Sushil K. Maurya and
• Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

• sequence of protection-deprotection-functionalization reactions at appropriate position (Figure 1). D-glucose, D-xylose and L-arabinose were used as the key starting materials for the DOS protocol. It was expected that each given sugar building block (generated in the building phase of the DOS) could be

• propargyl ether on the secondary OH group (1c). We have observed relatively low yields (3e and 3f) when we used a combination of glucose (1e and 2c) and xylose (1b and 2a) derived building block whereas an excellent yield was obtained (3g and 3h) when both coupling partners were derived from glucose (1e, 1d

• ), except when both building blocks contain a secondary azide and a secondary propargyl ether group (3c). Cycloaddition of building blocks derived from glucose and xylose worked better with non-protected OH groups (3i, 3j and 3k) than with protected (3e and 3f). Whereas glucose–glucose did work better with

A concise and practical stereoselective synthesis of ipragliflozin L-proline

• Shuai Ma,
• Zhenren Liu,
• Jing Pan,
• Shunli Zhang and
• Weicheng Zhou

Beilstein J. Org. Chem. 2017, 13, 1064–1070, doi:10.3762/bjoc.13.105

• Sodium-glucose co-transporter 2 (SGLT2) inhibitors are a new class of antidiabetes drugs, and dapagliflozin [1], canagliflozin [2], empagliflozin [3], ipragliflozin [4], tofogliflozin [5], luseogliflozin [6] have been approved for the treatment of Type 2 diabetes mellitus (T2DM). One of them

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

• Li Yang,
• Ping Wu,
• Jinghua Xue,
• Huitong Tan,
• Zheng Zhang and
• Xiaoyi Wei

Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103

• grown on the PDA medium at 28 °C for 10 days and 6 pieces of PDA culture plugs of the strain were inoculated into each of two 500 mL Erlenmeyer flasks containing 150 mL of seed medium (glucose 0.4%, malt extract 1.0%, yeast extract 0.4%, pH 5.5) and shaken on a rotatory (150 rpm) at 28 °C for 2 days

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

• the “thiol for thiol” ligand exchange method, which allows the superficial diversification by introducing small amounts of different ligands after the AuNP synthesis [11][12][18]. Recently, the Seeberger group reported a straightforward one-pot method to prepare glucose-stabilized ultrasmall AuNPs, by

• [69][70][71]. Moya and co-workers deeply studied the intracellular dynamics and aggregation of glucose-AuNPs by employing fluorescence correlation spectroscopy (FCS) [12]. They demonstrated that GAuNPs were ubiquitous distributed inside the cell as single NP or small aggregates, suggesting a strong

• binding properties of the glucose moiety displayed on a metal surface with insulin, a peptide hormone [86]. By means of a UV–vis spectroscopy assay, the authors confirmed the successful use of dextran-coated AuNPs to selectively bind low concentrations of insulin (at 1 pM), even in serum samples, and

Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

• Yan Chen,
• Xiaoman Wang,
• Junchang Wang and
• You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

• ; Introduction D-manno-Heptulose is a rare naturally occurring seven-carbon sugar first isolated from avocado [1], which exhibited promising diabetogenic effects through suppression of the glucose metabolism and insulin secretion via competitive inhibition of the glucokinase pathway [2][3][4][5][6]. Accordingly

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• of the esterified CDs was supported in Harada’s work [17] by comparing the NMR spectra with those obtained for a monoesterified β-cyclodextrin at C2 position (mono-2-O-(6-benzyloxypentanoyl)-β-cyclodextrin). The peak at 63.4 ppm was assigned as C2’ of the monosubstituted glucose ring belonging to

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

• iXon 888 EMCCD camera (1024 × 1024 pixels, Andor, Belfast, Northern Ireland) were used. N-Rh-DOPE was excited by a 561 nm diode laser. Fife µL GUVs were mixed with 15 µL 250 mM glucose buffer (5.8 mM NaH2PO4, 5.8 mM Na2HPO4, osmolarity of 300 mOsm/kg, pH 7.2) in tissue culture treated microscopy

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• ) chemical shift variations of the complex β-CD/2. Expansion of 2D-ROESY of 1/β-CD (left) and 2/β-CD (right) complexes. Atom numbering is referred to Figure 1. Primed numbers are used for glucose units. X-ray diffraction structures of 1/β-CD (top) and 2/β-CD (bottom) complexes. The distance between the

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

• Glucose-based fluorescent carbon dots Sustainable syntheses of CDs have driven researchers to find readily available, cheap and renewable carbon sources of which the monosaccharide glucose is an ideal candidate. Not only is glucose cheap and commercially available, but also has a low carbonisation

• glucose, this particular monosaccharide has been extensively used as an ideal carbon source for CD formation, under a range of experimental conditions. The microwave-assisted synthesis of FCDs from a glucose solution in the presence of poly(ethylene glycol)-200 (PEG-200) by Yang et al. is, to the best of

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• biological systems would evolve towards systems exhibiting maximum entropy production is contradicted by the high yield that is observed in the conversion of nutrients into cell components, as for instance during glucose metabolism. In this case entropy production only slightly exceeds the minimum required

Transition-metal-catalyzed synthesis of phenols and aryl thiols

• Yajun Liu,
• Shasha Liu and
• Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

• important roles in C–O coupling reactions for the synthesis of phenols from aryl halides. In 2011, the Sekar group used D-glucose as ligand and reported a Cu(OAc)2 catalyzed synthesis of phenols from aryl halides in the presence of KOH in DMSO/H2O (1:1) at 120 °C (Scheme 12) [34]. Aryl iodides and electron

• -deficient aryl bromides provided good to excellent yields. D-Glucose represents a type of environmentally friendly ligand and can be easily removed during the work-up process. This work is of special value as it was the first report employing copper(II) as the catalyst in the synthesis of phenols. In 2011

• of aryl halides using DMEDA as ligand. Hydroxylation of aryl halides using PAO as ligand. Hydroxylation of aryl halides using D-glucose as ligand. Hydroxylation of aryl halides using INDION-770 as ligand. PEG-400 mediated hydroxylation of aryl halides. Hydroxylation of aryl halides using glycolic

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• products confirm the characteristic signal pattern of a 6-substituted β-CD, having the C6 carbon atom of the substituted glucose unit shifted towards lower fields (42.27 ppm) (Figure S24 and Figure S32 in Supporting Information File 1). This chemical shift of the C6 carbon atom of the substituted glucose

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD⁺ analogues

• Sarah Wallrodt,
• Edward L. Simpson and
• Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

• tankyrases ARTD5 and ARTD6 also exhibit a unique domain structure consisting of multiple ankyrin repeats mediating protein–protein interactions [13]. Tankyrases are involved in telomere homeostasis, Wnt/β-catenin signalling, glucose metabolism, and cell cycle progression [14]. Remarkable efforts have been

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• investigate this possibility, we conducted a feeding experiment of [U-13C6]glucose which could label carbons derived from malonyl-CoA and hydroxymalonyl-ACP. In the 13C NMR spectrum, 13C–13C couplings were observed for C-1/C-2, C-3/C-4, C-5/C-6, C-7/C-8 in addition to the carbon pairs C-11/C-12, C-13/C-14, C

• -15/C-16, C-17/C-18, C-19/C-20, and C-21/C-22 (Table 1, Figure S3 in Supporting Information File 1). The 2D-INADEQUATE spectrum showed cross peaks for the above-mentioned two-carbon units derived from the glycolytic degradation of [U-13C6]glucose (Table 1, Figure 4b). Combined with the acetate

• experimentally identified the precursor of a tert-butyl group in a polyketide backbone. The unusual contiguous polyol system comprising eight hydroxylated carbons was proved to be arising from the chain extension using hydroxymalonyl-ACP by labeling experiments of [1,2-13C2]acetate and [U-13C6]glucose. This

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• monofunctionalized derivatives. However, the synergistic effect was regiodependent and only observed with the imidazole substituent located in position 2 of one methylated glucose unit and the α nucleophile in position 3 of the adjacent methylated glucose unit (compound 1, Figure 2). Herein we present an extended

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

• Peter H. Seeberger,
• Claney L. Pereira and
• Subramanian Govindan

Beilstein J. Org. Chem. 2017, 13, 164–173, doi:10.3762/bjoc.13.19

• unselective β-mannoside formation step we resorted to glucose–mannose conversion by inversion of the C2 stereocenter following selective installation of a trans-glucosidic linkage. Differentially protected thioglucoside 11 [22] is equipped with a participating C2 levulinyl ester that is replaced by an axial

Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds

• Cira Mollings Puentes and
• Thomas J. Wenzel

Beilstein J. Org. Chem. 2017, 13, 43–53, doi:10.3762/bjoc.13.6

• . Cyclodextrins (CDs), which are cyclic oligosaccharides containing D-glucose units, represent an important and versatile class of chiral NMR solvating agents (Figure 1). The most common representatives are α-, β- and γ-CD, which contain six, seven and eight glucose rings, respectively. Many substrates form

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• children, results in severe hepatosplenomegaly and neurodegeneration [3][6]. Hence, the sequestration of cholesterol is an important factor in the development of the NPC disease. Cyclodextrins (CDs) are cyclic glucose oligosaccharides used by the pharmaceutical industry to enhance solubility, stability

• , corresponding to tri-, tetra-, penta-, hexa- and hepta-lactose-substituted β-CDs, respectively (Figure 2A). Further, the 1H NMR spectrum indicated that the degree of substitution of lactose (DSL) was 5.6. This value was obtained from the integral values of the anomeric protons of lactose and glucose in β-CD

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• oligosaccharides consisting of 6–8 glucose units (α-, β- and γ-CD) primarily used in the pharmaceutical, cosmetic and household chemical industry [8]. They form non-covalent inclusion complexes with a great number of the organic contaminants in soil (petroleum hydrocarbons, polycyclic aromatic hydrocarbons, etc

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• electron supply to the P450s (Figure 3) [38]. NADH was additionally regenerated throughout the assay via a glucose/glucose oxidase couple. The assay was stopped by cleaving the peptide from the PCP-X constructs using excess of methylamine and the peptide was then purified by solid phase extraction before

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

• measurements, the binding constants can be estimated. The obtained results reveal that D-ribose, D- and L-arabinose, D-xylose, D-lyxose, D-2-deoxyribose, and methyl β-D-ribopyranoside were complexed by β-CD (binding constants ≤14 M−1). In contrast, aldohexoses and their derivatives (D-glucose, D-galactose, D

• important for determining the structure and for the selectivity of the complex. It is noteworthy that several other publications have studied the interaction of D-glucose with native CDs. For instance, Hirsh and co-workers estimated the binding constants of D-glucose to α-CD and β-CD at 450 and 420 M−1

• , respectively, from blood glucose meter [96]. In contrast, Hacket et al. determined the binding constant of D-glucose to β-CD at 0.6 M−1 by fluorimetric competition titrations [97]. The results obtained by Hacket et al. are closer to the values published by Aoyama and co-workers. In addition, it is quite

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

• Michał Malik and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

• subsequent syn-dihydroxylation with the re-use of Ru catalyst. These transformations applied to optically pure 4,5,6-tribenzyloxycyclohexenone 17 derived from D-glucose gave the desired bicyclic structures in good yields and very good diastereoselectivities. To sum up, the proposed methodology is an