Synthesis of Oligosaccharides on Soluble High-Molecular-Weight Branched Polymers in Combination with Purification by Nanofiltration

Abstract

[structure: see text] An efficient approach for polymer-supported oligosaccharide synthesis is described whereby branched and high-molecular-weight PEG derivatives are used in combination with purification by nanofiltration. This methodology was applied to the preparation of a tetraglucoside and the tumor-associated antigen Le(x).

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

“…476–478 Alternatively, nanofiltration or a size-exclusion separation offer other possible alternatives for separation of polymer-bound molecules and the rest of the reaction components. 479 An elegant synthesis that combines advantages of the soluble polymer-supported technology and convergent building block strategy was applied to the synthesis of hexasaccharide 100 (Scheme 21). 480 In this application, fluorenylmethoxycarbonyl (Fmoc) and diethylisopropylsilyl (DEIPS) are used as temporary substituents that could be removed with Et 3 N and TBAF, respectively, without affecting the linker.…”

Typical pharmaceutical molecule removal behavior from water by positively and negatively charged composite hollow fiber nanofiltration membranes

“…38 However, the rejection rates of the noroxacin with higher MW decreased slightly. 39,40 The decline of the pharmaceutical rejection rate was different for the PEI-NF and PIP-NF membrane. This phenomenon may be attributed to the intrapore viscosity of the pharmaceutical molecules varying with the membrane structure and pharmaceutical conformation.…”

Oligosaccharide synthesis on soluble high-molecular weight pHEMA using a photo-cleavable linker

“…Poly(ethylene glycol)methyl ether (mPEG) has been the most widely used as a soluble polymer for oligosaccharide synthesis. 17–21 In recent years, other soluble polymers such as polystyrene, 22 polyvinyl alcohol (PVA), 23 and hyper-branched polyethylene glycol (PEG) 24 have been utilized for oligosaccharide synthesis.…”

“…For example, a variety of donors such as trichloroacetimidates, 31,32 sulfoxides, 33 glycals 34,35 and pentenyl glycosides 36 have been successfully employed in soluble polymer-supported oligosaccharide syntheses. In this study, we used thioglycoside donors 24 because of their long shelf life and ease of preparation.…”