270075-72-4Relevant articles and documents
Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach
Nilsson, Inga,Michalik, Dirk,Silipo, Alba,Molinaro, Antonio,Vogel, Christian
, p. 98 - 107 (2015/03/05)
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
Mechanistic studies and methods to prevent aglycon transfer of thioglycosides
Li, Zhitao,Gildersleeve, Jeffrey C.
, p. 11612 - 11619 (2007/10/03)
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.
A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide
Pozsgay, Vince
, p. 151 - 172 (2007/10/03)
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