Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• properties leading to a host–guest relationship with organic substances [6][7][8][9]. These cyclic oligosaccharides are water soluble in their native form and are often modified to prepare novel insoluble CD-based materials. Two patents published by Martel et al. [10], and Trotta et al. [11] can be consulted

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

• Mei-Yuan Hsu,
• Yi-Pei Liu,
• Sarah Lam,
• Su-Ching Lin and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

• [4], and were recently observed to inhibit cancer growth [5]. Because of the relevance of 2-deoxyglycosides, great efforts have been made in researching the assembly of oligosaccharides containing these sugars [6][7]. However, the absence of a neighbouring group at C2 causes poor stereoselectivity

• anomeric mixtures [10]. Glycals have been considered as alternative precursors for producing 2-deoxythioglycosides as well as oligosaccharides. Several methods based on the use of glycals in the presence of Lewis acids for S- or O-2-deoxyglycoside preparations have been developed [51][52][53][54][55][56

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

• Markus W. Weishaupt,
• Stefan Matthies,
• Mattan Hurevich,
• Claney L. Pereira,
• Heung Sik Hahm and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

• step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides. Keywords: automation; glycosylation; protecting groups

• ; oligosaccharides; solid-phase synthesis; Streptococcus pneumoniae; Introduction The Gram-positive encapsulated commensal bacterium Streptococcus pneumoniae [1][2][3] can cause serious medical conditions like pneumonia, meningitis, endocarditis and sepsis [4]. S. pneumoniae is the leading cause of vaccine

• containing oligosaccharides of different lengths and frame shifts [19]. Synthetic oligosaccharide antigens enable structure–activity relationship (SAR) studies of bacterial antigens [20] to better understand antibody binding and help to improve existing vaccine formulations. Two synthetic routes to prepare

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

• . The polymers (oligosaccharides) of D-glucose found, for example, in wood (cellulose) and D-glucosamine present in shells of crabs and insects (chitin), are the widely known ones [1][2]. Another class of carbohydrate biopolymer derivatives – D-ribose and 2-deoxy-D-ribose – constitutes the backbone of

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

• Štěpán Horník,
• Lucie Červenková Šťastná,
• Petra Cuřínová,
• Jan Sýkora,
• Kateřina Káňová,
• Roman Hrstka,
• Ivana Císařová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

• analogs 6–8 are new compounds and their influence on the cell-surface glycan biosynthesis is currently being studied. We anticipate that 1,6-anhydro-2-azido-fluorohydrins 20, 21, 26 and 31 will find use as building blocks for the synthesis of fluorinated oligosaccharides and other glycoconjugates because

Elucidation of a masked repeating structure of the O-specific polysaccharide of the halotolerant soil bacteria Azospirillum halopraeferens Au4

• Elena N. Sigida,
• Yuliya P. Fedonenko,
• Alexander S. Shashkov,
• Nikolay P. Arbatsky,
• Evelina L. Zdorovenko,
• Svetlana A. Konnova,
• Vladimir V. Ignatov and
• Yuriy A. Knirel

Beilstein J. Org. Chem. 2016, 12, 636–642, doi:10.3762/bjoc.12.62

• above), elimination of the side-chain Glc and cleavage of the linkage of the destroyed 2-substituted Xyl were expected. Fractionation of the Smith degradation products by TSK HW-40 (S) gel-permeation chromatography resulted in a mixture of the expected oligosaccharides 1 and 2 and higher molecular mass

• published data δ 72.3 and 76.8 for α- and β-Glc, respectively [19]. The 4-substitution of Fuc was inferred from a significantly downfield shift to δ 82.1–83.0 of the C-4 signal as compared with its positions in the non-substituted α-Fuc at δ 72.9 [19]. Combining structural data of the oligosaccharides 1–3

• afforded complementary oligosaccharides, which identification shed light on the nature of the OPS irregularity and, combined with chemical analysis and NMR spectroscopic analysis data, enabled the structure elucidation of the OPS. Chemical modifications of the OPS, such as O-methylation or O-acetylation

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• ][6][7]. CDs are a family of cyclic oligosaccharides and different members of this family have been used widely for several years. More specifically, CDs are manufactured from starch, a polymer with D-glucopyranoside building blocks with both α-1,4- and α-1,6-glycosidic linkages [8]. The most common

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization. Keywords: DMT-MM; fluorescein; rhodamine; supramolecular assembly; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides consisting of 6, 7 or 8

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

• environment only. The secondary carbon substitution results in inversion in the reaction centre which changes the sugar moiety from glucoside to mannoside, altroside or alloside making those derivatives CD-based cyclic oligosaccharides and not CDs. The design of green synthetic methods for the bulk

• Vijayalakshmi have pointed out the theoretical use of enzymes in the production of CDs or other cyclic oligosaccharides, like cyclofructan, rather than using a microreactor [104]. Conclusion Dynamic intrusion of the enabling technologies to the CD chemistry is inevitable and shows exponential growth. Although

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• ) the hydrolysis of the nerve agents by CDs under specific conditions; (3) the selective modifications of these cyclic oligosaccharides to improve their hydrolytic efficiency at physiological pH and temperature. Review Inclusion studies between CDs and pesticides Due to their toroidal structure, CDs are

• cyclic oligosaccharides. As CDs exhibit a large number of primary (C-6 position of glucose units) and secondary (C-2 and C-3 positions) alcohols, selective modifications are therefore difficult. Most of them are based on the slight differences in the reactivity of these three kinds of hydroxy groups. In

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

• -containing microcapsules [27][33] and spontaneous emulsification for obtaining nanoemulsions [20][31][32]. One nanoencapsulation method of fish oil components is the molecular encapsulation in cyclodextrins (CDs). The latter are natural or synthetically modified, cyclic oligosaccharides comprising 6, 7, and

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

• ], chemical sensors [6] and drug delivery [7][8][9]. As discussed in a range of reviews [10][11][12][13][14] and books [15][16][17][18], cyclodextrins are naturally occurring cyclic oligosaccharides which are also produced industrially through the enzymatic metabolism of starch and related compounds. The

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• cyclic oligosaccharides. The common native CDs contain 6, 7 and 8 D-(+)-glucopyranose units bound together by α(1→4) linkages and are referred to as α-, β- and γ-CDs [21]. The chair conformation of the glucose units results in a truncated shape of CDs with an external hydrophilic surface and a

Assembly of synthetic Aβ miniamyloids on polyol templates

• Sebastian Nils Fischer and
• Armin Geyer

Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284

• diols on the template must be separated from each other far enough to exclude the simultaneous formation of mixtures of 5- and 6-membered boronic esters. However, the oligosaccharides, which are available with a consistent oligomerization degree of dimer, trimer, tetramer and higher, are known to have

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• oligosaccharides, which have subnanometer-sized cavities where guest molecules with an appropriate size and shape are incorporated [10]. CDs have been reported to work as emulsion stabilizers [11][12][13][14]. Previous studies have shown that CDs can form surface-active inclusion complexes with oil molecules at

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

• Chompoonut Rungnim,
• Sarunya Phunpee,
• Manaschai Kunaseth,
• Supawadee Namuangruk,
• Kanin Rungsardthong,
• Thanyada Rungrotmongkol and
• Uracha Ruktanonchai

Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251

• addition [2][3][4][5][6][7][8] and surfactant addition [9]. Complexation is one of the most utilized methods for enhancing the solubility of poorly soluble drugs. Cyclodextrins (CDs) are well-known macrocyclic oligosaccharides that are produced by enzymatic degradation of starch. CDs consist of 6, 7 and 8

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

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

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• cholesterol sequestration is found to be a crucial factor in developing NPC disease. Cyclodextrins (CyDs) are non-reducing cyclic glucose oligosaccharides obtained by enzymatic means from starch-containing raw materials and have been used for the enhancement of drugs solubility, stability and bioavailability

Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst

• Redouane Beniazza,
• Natalia Bayo,
• Florian Molton,
• Carole Duboc,
• Stéphane Massip,
• Nathan McClenaghan,
• Dominique Lastécouères and
• Jean-Marc Vincent

Beilstein J. Org. Chem. 2015, 11, 1950–1959, doi:10.3762/bjoc.11.211

• such transformations are: (i) high copper loading, often used in excess with respect to the substrates, due to limited catalyst reactivity and the fact that the substrates (proteins, oligonucleotides or oligosaccharides) are typically used in dilute conditions; (ii) contamination of the products by

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• singlet at δ = 7.78 ppm confirming the cycloaddition of derivatives 3 and 10. D-Glucosamine is an essential constituent of many naturally occurring oligosaccharides such as bacterial and fungal cell walls. Mainly, it is available as N-acetylglucosamine in β-glycosidic linkages (β-D-GlcNAc) [37

Profluorescent substrates for the screening of olefin metathesis catalysts

• Raphael Reuter and
• Thomas R. Ward

Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203

• quencher are disconnected resulting in the fluorescent product 7. A similar linker concept has previously been implemented for a solid-phase linker in the synthesis of oligosaccharides [18][19]. The second profluorescent molecule selected was diolefin 8, which yields fluorescent 7-hydroxycoumarin

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

• Maroš Bella,
• Miroslav Koóš and
• Chun-Hung Lin

Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170

• of enzymes that are responsible for the biosynthesis of complex oligosaccharides, glycoproteins and other glycoconjugates in mammalian biological systems. These glycoconjugates are operating in the cell and on the cell surface, particularly as glycoproteins, and are involved in many vital biological

• unknown [7]. In general, GTs transfer sugar nucleotide donors onto suitable acceptors during the biosynthesis of glycans and glycoconjugates [8]. Both donor and acceptor substrates are recognized by GTs binding pockets. For instance, in the course of biosynthesis of complex and hybrid oligosaccharides

Automated solid-phase synthesis of oligosaccharides containing sialic acids

• Chian-Hui Lai,
• Heung Sik Hahm,
• Chien-Fu Liang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2015, 11, 617–621, doi:10.3762/bjoc.11.69

• 10.3762/bjoc.11.69 Abstract A sialic acid glycosyl phosphate building block was designed and synthesized. This building block was used to prepare α-sialylated oligosaccharides by automated solid-phase synthesis selectively. Keywords: α-sialylation; automated synthesis; glycosylation; sialic acid; solid

• carbohydrate antigens (TACAs) such as the sialyl-Tn antigen (sTn) [2]. Neu5Ac is often the terminal residue and is usually linked via an α-(2,3) or α-(2,6) linkage to galactose (Gal) (Figure 1) [3]. Automated glycan assembly enables rapid access to structurally defined oligosaccharides [4][5] including

• incorporation of sialic acid–galactose disaccharide building blocks [5][11]. Here, we describe a sialic acid building block that can be utilized for automated glycan assembly. Results and Discussion Sialylating oligosaccharides in high yield and α-selectivity was challenging since the presence of a C-1 carboxyl

Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more

• Marina Bantzi,
• Stephan Rigol and
• Athanassios Giannis

Beilstein J. Org. Chem. 2015, 11, 604–607, doi:10.3762/bjoc.11.67

• fragments which were bearing either a free reducing end or a non-functionalized aglycone [16][17][18]. In 2007, a study focusing on the synthesis of HA sequences which could be functionalized and used for biological studies yielded oligosaccharides bearing an alkyl-azide [19]. Besides the results of this

• linkages; most important was the reaction's stereochemical outcome. Elongation of the synthesized oligosaccharides was easily done, since the TBS-protection is selectively cleavable. The anomeric allyl moiety permits varieties of feasible modifications including the introduction of an azido group. In the

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

• CPT for cancer therapy. CDs can be a means of overcoming these problems for the in vivo behaviour of CPT upon intravenous or oral administration. CDs are natural polymers which are produced from enzymatic degradation of starch [23]. They are cyclic oligosaccharides and consist of at least 6 D

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• ethanol, because they could not be dissolved in water owing to their long alkyl chains. However, solubilization of PUFAs could also be achieved by aqueous cyclodextrin (CD) solutions, which allowed us to avoid organic solvents. CDs are cyclic oligosaccharides consisting of 6, 7 or 8 glucopyranose units (α