The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• drugs as amphiphilic assemblies, sugar recognition and subsequent excretion should be reduced [40][41][42]. Sugar-based amphiphiles are often termed glycolipids and are also of interest for their use as ‘green’ surfactants in household cleaning products [43]. Previous work in this field has been

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• ; ricin; Introduction Carbohydrate-binding proteins (lectins) and proteotoxins, e.g., verotoxins [1][2] and cholera toxins [3], can cause serious damages to human cells. The carbohydrate binding proteins are able to interact with cell-surface glycoconjugates such as glycoproteins and glycolipids to

• attempts of applying these glycomaterials for both the detection and the decontamination of biological toxins in an assumed polluted scene [19][20][21]. In the present study, we attempted to apply our N-glycosyl-[60]fullerenes [22][23][24][25], which were designed as a novel class of glycolipids with

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

• and glycolipids on the cell surface. Sialic acids are involved in the communication of cells with their environment [41] and selective detection, binding and blocking of sialic acids on the cell surface is of significant biomedical interest. It is the aim of this report to investigate whether the

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

• Alafia A. Ansari,
• Y. Suman Reddy and
• Yashwant D. Vankar

Beilstein J. Org. Chem. 2014, 10, 300–306, doi:10.3762/bjoc.10.27

• obtained the α-C-glycosides in an efficient manner, we explored their synthetic utility to synthesize a 2-deoxy-2-amino-α-C-glycoside. 2-Deoxy-2-amino-α-C-glycosides have received considerable attention in recent years due to their use in the synthesis of glycopeptides [50][51], glycolipids [51] and

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

• Tamashree Ghosh,
• Abhishek Santra and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

• various thiooligosaccharides, glycoproteins and glycolipids [28][29][30][31][32]. The anomeric configurations of glycosyl thiols mostly remain unaffected in comparison to the glycosyl hemiacetal derivatives during their synthetic transformations [4]. Glycosyl thiol derivatives act as precursors for the

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• ; carbohydrate elongation; non-natural carbohydrate conjugates; Introduction Glycoconjugates such as glycoproteins, glycopeptides, glycolipids and peptidoglycans are ubiquitous in nature [1]. They are found on cell surfaces and are responsible for processes such as cell–cell interaction, recognition and

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• development of drug-delivery systems [3]. Synthetic bilayer vesicles are a versatile model for biological cell membranes, and there are a substantial number of reports on synthetic glycolipids that mimic the glycocalyx [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. Multivalent

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• , classifications, and information regarding related diseases. GlycoEpitopeDB provides information on antibodies that recognize specific carbohydrate epitopes and glycoproteins or glycolipids that are known to carry the epitopes. A frequently used technique to study the epitopes, to which a GBP binds, are glycan

• structures stored in the databases. An analysis of mammalian carbohydrate structures present in Glycosciences.DB, for example, revealed that this data set contained 3299 oligosaccharides, which are part of N-glycans, O-glycans or glycolipids from 38 mammalian species. Only ten different monosaccharides were

• glycoproteins, protein–carbohydrate complexes, or glycolipids, the force fields have to cover all types of molecules involved [100][120]. The force fields need to be extensible if not only standard monosaccharides, but also derivatized residues are included in a simulation, which is especially important during

Chemo-enzymatic modification of poly-N-acetyllactosamine (LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) based on galactose oxidase treatment

• Christiane E. Kupper,
• Ruben R. Rosencrantz,
• Birgit Henßen,
• Helena Pelantová,
• Stephan Thönes,
• Anna Drozdová,
• Vladimir Křen and
• Lothar Elling

Beilstein J. Org. Chem. 2012, 8, 712–725, doi:10.3762/bjoc.8.80

• epitopes on glycoproteins and glycolipids are based on N-acetyllactosamine units (LacNAc; Galβ1,4GlcNAc) and often present on extended poly-LacNAc glycans ([Galβ1,4GlcNAc]n). Poly-LacNAc itself has been identified as a binding motif of galectins, an important class of lectins with functions in immune

• of poly-LacNAc oligomers was utilised for the reductive amination of 6-aldehyde groups of oxidised poly-LacNAc oligomers (Scheme 4). In this way, chemically branched poly-LacNAc glycans are synthesised that resemble natural, branched poly-LacNAc glycans (I-antigens) of glycoproteins and glycolipids

An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens

• Yoshihiro Nishida,
• Yuko Shingu,
• Yuan Mengfei,
• Kazuo Fukuda,
• Hirofumi Dohi,
• Sachie Matsuda and
• Kazuhiro Matsuda

Beilstein J. Org. Chem. 2012, 8, 629–639, doi:10.3762/bjoc.8.70

• %) conformers around the lipid tail, while adopting all of the three conformers with equal probability around the sugar position. This property was very close to what we have observed with respect to the conformation of phosphatidylcholine (DPPC), suggesting that the Mycoplasma glycolipids GGPLs may constitute

• . They are suspected to be associated with human immune diseases, in either direct or indirect ways, although the molecular mechanism is not fully understood [1]. In recent biochemical studies, Mycoplasma outer-membrane lipoproteins [2][3] and glycolipids [4][5][6] are thought to serve not only as the

• and characterized by other groups [11][12][13][14]. Absolute chemical structures of GGPL-I [15] and GGPL–III [16] have already been established by chemical syntheses of stereoisomers; these α-glycolipids have a common chemical backbone of 3-O-(α-D-glucopyranosyl)-sn-glycerol carrying phosphocholine at

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• functionalization of the anomeric position and the 4- and 6-hydroxy groups. We have found that further derivatization of the glucose headgroup to form different glycolipids can result in organogelators [34][35][36][37]. Previously, we have systematically synthesized and studied the self-assembling properties of a

• synthesized the terminal acetylenes 9–11, saturated hydrocarbons 12–14, aryl derivatives 15,16, and two long chain diacetylene containing glycolipids 17,18. After we obtained these compounds, we then screened them for gelation in several solvents. These results are shown in Table 1. From the gelation test

• used headgroup 1 to synthesize a library of diacetylene containing lipids, and found that many of them are effective gelators [35]. Using the headgroup 8, we also synthesized six long chain diacetylene containing glycolipids 17A–17C and 18A–18C. We found that the diesters are effective gelators for

Carbasugar analogues of galactofuranosides: α-O-linked derivatives

• Jens Frigell and
• Ian Cumpstey

Beilstein J. Org. Chem. 2010, 6, 1127–1131, doi:10.3762/bjoc.6.129

• oligosaccharides, including plant polysaccharides [5], fungal cell wall polysaccharides [6], glycolipids from thermophilic bacteria [7] and glycosphingolipids from marine sponge (agelagalastatin) [8]. Moreover, the precursor to β-galactofuranosides and the substrate for galactofuranosyltransferases is UDP

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• glycan structures of various types forming the individual, dynamic glycocalyx of each cell type. These glycolipids and glycoproteins often carry sialic acids, in humans N-acetylneuraminic acid (Neu5Ac, 1, Scheme 1), at their terminal position which mediate cell-cell recognition and signal transduction

• with HEp-2 cells. Ac4GlcNAz 16 is believed to enter the cell by diffusion through the membrane, to undergo deacetylation in the cytoplasm and then incorporated into the cell surface glycoproteins and glycolipids. Alternatively, it is metabolically converted to Neu5Az [14]. Neu5Hex may enter the cell by