- Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach
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To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-l-rhamnopyranosyl-(1→2)-α-d-galactopyranosyl-(1→3)-α-l-rham
- Nilsson, Inga,Michalik, Dirk,Silipo, Alba,Molinaro, Antonio,Vogel, Christian
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- Facile synthesis of biotin-labelled α-galactosylceramide as antigen for invariant natural killer T cells
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When iNKT cells are stimulated by the CD1d presented exogenous α-galactosylceramide, a myriad of cytokines are released that trigger a variety of immune responses. However, the invisibility and poor aqueous solubility of α-galactosylceramide during bioass
- Xia, Chengfeng,Zhang, Wenpeng,Zhang, Yalong,Woodward, Robert L.,Wang, Jinhua,Wang, Peng G.
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experimental part
p. 6390 - 6395
(2009/12/06)
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- Mechanistic studies and methods to prevent aglycon transfer of thioglycosides
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Thioglycosides have been employed extensively for the synthesis of complex oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful, aglycon transfer is a problematic side reaction with thioglycosides. In this paper, a series of mechanistic studies are described. The aglycon transfer process is shown to affect both armed and disarmed thioglycosides, cause anomerization of the carbon-sulfur bond of a thioglycoside, and destroy the product of a glycosylation reaction. The results indicate that the aglycon transfer process can be a major problem for a wide range of thioglycosides. This side reaction is especially important to consider when carrying out complex reactions such as solid-phase glycosylations, one-pot or orthogonal multicomponent glycosylations, and construction of carbohydrate libraries. To prevent transfer, a number of modified aglycons were examined. The 2,6-dimethylphenyl (DMP) aglycon was found to effectively block transfer in a variety of model studies and glycosylation reactions. The DMP group can be installed in one step from a commercially available thiol (2,6- dimethylthiophenol) and is useable as a glycosyl donor. On the basis of these features, the DMP group is proposed as a convenient and improved aglycon for thioglycosides.
- Li, Zhitao,Gildersleeve, Jeffrey C.
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p. 11612 - 11619
(2007/10/03)
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- Approaches to intramolecular sialylation 1. Synthesis of pseudodisaccharide Neu5Ac-(1-2)-Gal with ester-linked monosaccharide residues
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An efficient approach was developed for ester-linking the sterically hindered carboxy group of N-acetylneuraminic acid with the secondary hydroxy group at C(2) of galactose. Putative precursors of the glycosidically linked disaccharide Neu5Ac-(2-3)-Gal we
- Kononov,Volodin,Magnusson
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p. 1434 - 1441
(2007/10/03)
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- A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide
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The use of lipophilic, acyl-type protecting groups in the synthesis of higher-membered oligosaccharides is described by the example of oligosaccharides corresponding to the O-specific polysaccharide (O-SP) of Shigella dysenteriae type 1. Thus, O-stearoyla
- Pozsgay, Vince
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p. 151 - 172
(2007/10/03)
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- PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES
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Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus
- Fernandez-Mayoralas, Alfonso,Marra, Alberto,Trumtel, Michel,Veyrieres, Alain,Sinay, Pierre
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