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

• glucose and galactose moieties multi-displayed on gold surface acted as target for asialoglycoprotein receptors, over-expressed on liver cancer cells, delivering selectively the anticancer drug Au(I). In search of novel antimicrobial antigens, chitosan-streptomycin GAuNPs (CA NPs), i.e., carbohydrate

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

• [13][24]. Similarly, important carbohydrate-based biopolymers such as cellulose, chitin, chitosan, dextran, cyclodextrin, and hyaluronic acid, which differ not only in elemental composition, but also in chemo-physical properties, have also been successfully utilised in the preparation of CDs, where

• , readily available neutral carbohydrate such as glucose as the carbon source in combination with a nitrogen-containing molecule. Glucosamine hydrochloride, which is a byproduct from the hydrolysis of chitosan and chitin polysaccharides found on crustacean shells, bears an amine functionality at C-2 and

• -derived CDs, the different features and functional groups present in those distinct carbohydrate chains, will have an effect in the final properties of the CDs synthesised from them. Pramanik et al. exploited this hypothesis in the synthesis of CDs from three different polysaccharides: chitosan (Chi-CDs

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• negative controls. As positive control, we used chitosan (β-1,4 linked glucosamine) with average molecular weight, a fungal elicitor with known effect as NO and ROS inductor on A. thaliana [61]. Intracellular ROS was visualized using 2’,7’-dichlorodihydrofluorescein diacetate (H2DCF DA) as fluorescence

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• and sugar moieties were described before [22][25][26]. It was shown that quaternization of chitosan increases its antimicrobial activity; such polymer is proposed to be used as a wound dressing after surgeries to eliminate infections and to improve the healing process [27][28][29]. Moreover, the

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• interaction and may promote the formation of metal nanoparticle clustering. Cu(I)-based system have been used in alkyne/azide [3 + 2] cycloadditions, while Pd(II)-based catalysts have been used in C–C couplings reactions (Scheme 7) [34]. An example of water-soluble β- and γ-CD/chitosan derivatives have been

• studied for binding Gd(III) chelates that bear hydrophobic substituents and negative charges [35]. These bio-polymers were easily prepared in two reaction steps by reacting CDs with maleic anhydride followed by activation with carbodiimide to form amide linkages with amino groups of chitosan. The

• esterification of CD was promoted by MW irradiation, while the chitosan coupling used a water-soluble carbodiimide, N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, under US. A mild sonication at rt using HDI enabled efficient CDs reticulation in the presence of lipases (Scheme 7) whose biocatalytic

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

• Daniel I. Hădărugă,
• Mustafa Ünlüsayin,
• Alexandra T. Gruia,
• Cristina Birău (Mitroi),
• Gerlinde Rusu and
• Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

• various matrices. Matrices such as chitosan and N-lauroyl chitosan [25], N-stearoyl-O-butylglycerylchitosan [26], mixtures of soybean soluble polysaccharide and octenyl succinic anhydride [27], hydrolyzed soy protein isolate and maltodextrin [20][28], liposomes [29] and even yeast cell autolysate [30

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• network formed when host–guest complexation occurs. In earlier studies, Auzély-Vetly et al. reported the substitution of chitosan (molecular weight 195 kDa) with adamantyl groups and characterized their complexation in the β-CD annuli of a singly octamethylene-linked β-CD dimer b and a doubly

• -substituted chitosan showed a moderate increase in viscosity with increase in β-CD dimer b concentration at a constant substituted-chitosan concentration consistent with the formation of cross-links forming through ditopic complexation by the β-CD dimer b of adamantyl substituents on adjacent chitosan chains

• -substituted chitosan and the diamino-poly(ethylene glycol)-linked adamantyl dimer e and the poly(ethylene glycol)-linked adamantyl dimer f, in which the linker molecular weight is either 3.4 or 20 kDa in each case, shown in Figure 10d, e and f, respectively [81]. Rheological studies of aqueous solutions of β

Multivalent dendritic polyglycerolamine with arginine and histidine end groups for efficient siRNA transfection

• Fatemeh Sheikhi Mehrabadi,
• Hanxiang Zeng,
• Mark Johnson,
• Cathleen Schlesener,
• Zhibin Guan and
• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 763–772, doi:10.3762/bjoc.11.86

• biomedical purposes [6] such as anti-inflammatory [10] and anticancer therapy [11][12]. Previously a number of cationic polymers like chitosan [13][14][15], PEI [16], and PAMAM [17] have been post-modified with histidine (His) or arginine (Arg) groups. The introduction of histidine groups has been beneficial

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• immobilization of an enzyme on the electrode covered with different conducting polymers often embedded with carbon nanotubes and/or metal nanoparticles [52][53][54][55][56]. Chitosan, a naturally occurring biopolymer, has also been utilized for sensor fabrication [57][58]. Cholesterol oxidase has been

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• reason, an amphiphilic cyclodextrin (CD) derivative per-modified on the primary face 6OCAPRO was used as core molecule to form nanocapsules with the nanoprecipitation technique. Nanocapsules were further coated with the cationic polymer chitosan to improve the cellular uptake and interaction with

• nanocapsules were then coated with the cationic polymer chitosan to improve the cellular uptake and interaction with biological membranes and penetration through intestinal mucosa for absorption of CPT and reaching the circulation. Nanocapsules were characterized for their in vitro properties followed by cell

• a negative surface charge of −11 mV on the surface as compared with chitosan-coated cationic nanocapsules (CS-CD) that have a charge of +10 mV. The zeta potential of chitosan coated CD nanocapsules was significantly higher than uncoated CD nanocapsules (P < 0.05) due to the positive charge of CS

A promising cellulose-based polyzwitterion with pH-sensitive charges

• Thomas Elschner and
• Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

• . While polyzwitterions based on N-functionalized chitosan [14][15] or 6-desoxy-6-aminocelluloses [16] are composed like synthetic polybetaines, a few cellulose-based zwitterions are described where the isoelectric point and the properties in solution could be tuned by varying the substitution pattern [17

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• have been focused on polysaccharides or on carbohydrates linked to proteins. A review dedicated to PEGylated chitosan derivatives has been published [22]. In the present review we present different approaches used for modification of glycans by covalent conjugation with PEG reagents, in particular with

• identification of signals that disappear or are shifted when conjugation takes place, together with the appearance of new signals due to the sugar in well-separated regions of the spectrum are used to confirm the extent of derivatization of the multiarm PEGs. PEGylation of polysaccharides: PEGylation of chitosan

• and chitosan derivatives for pharmaceutical applications was described [22]. Chitosan is the polysaccharide obtained from the abundant chitin by alkali or enzymatic degradation. It consists of a backbone of β-(1→4)-linked D-glucosamine units with a variable degree of N-acetylation. The protonated

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

C–C Bond formation catalyzed by natural gelatin and collagen proteins

• Dennis Kühbeck,
• Basab Bijayi Dhar,
• Eva-Maria Schön,
• Carlos Cativiela,
• Vicente Gotor-Fernández and
• David Díaz Díaz

Beilstein J. Org. Chem. 2013, 9, 1111–1118, doi:10.3762/bjoc.9.123

• other biocatalysts shows an increase of the first-order rate constant in the order chitosan < gelatin < bovine serum albumin (BSA) < collagen. The results of this study indicate that simple edible gelatin can promote C–C bond forming reactions under physiological conditions, which may have important

• salmon testes DNA [11] and chitosan [12], as well as various enzymes [13][14][15][16], have been reported to catalyze this type of reaction. However, to the best of our knowledge, the role of natural gelatin or collagen proteins as potential biocatalysts for C–C bond formation has not been yet described

• meaningful comparison with other known biocatalytic systems (i.e., chitosan [29], bovine serum albumin (BSA) [30][31]) we carried out the kinetic analysis of the model reaction for each case [8]. Figure 2 shows the first-order kinetics plots demonstrating the fine-tuning of the reaction rate in response to

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

Phytoalexins of the Pyrinae: Biphenyls and dibenzofurans

• Cornelia Chizzali and
• Ludger Beerhues

Beilstein J. Org. Chem. 2012, 8, 613–620, doi:10.3762/bjoc.8.68

• the type of elicitor added [23]. Yeast extract mainly induced the formation of aucuparin (3), whereas chitosan, although being a relatively poor elicitor, primarily stimulated the production of noraucuparin (2). Maximum phytoalexin levels were observed after the addition of autoclaved suspensions of

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• g∙mol−1 were measured. Another group reported the reaction between chitosan oligosaccharide with ethylene glycol diglycidyl ether to encapsulate paclitaxel in methylene dichloride-water miniemulsions [99]. The encapsulation was determined by HPLC to be between ~84% and ~92% depending on the ratio

Novel multi-responsive P2VP-block-PNIPAAm block copolymers via nitroxide-mediated radical polymerization

• Cathrin Corten,
• Katja Kretschmer and
• Dirk Kuckling

Beilstein J. Org. Chem. 2010, 6, 756–765, doi:10.3762/bjoc.6.89

• ) chloride, well-defined PNIPAAm could be synthesized at room temperature [27]. Several graft copolymers are described in previous reports such as Chitosan-graft-PNIPAAm [28] and PNIPAAm-graft-P2VP polymers [29]. Both polymers show a temperature- and pH-responsive phase behavior in aqueous solutions. While