Ionic catch and release oligosaccharide synthesis (ICROS)

Abstract

A general and efficient chromatography-free ionic-liquid-supported "catch-and-release" strategy for oligosaccharide synthesis (ICROS) is reported. The methodology is compatible with current glycosylation strategies and amenable to protecting group manipulations. A series of β-(1→6) and β-(1→2)-linked glycan structures have been prepared to showcase the versatility of the strategy.

In vitro biosynthesis of poly-β-1,4-glucan derivatives using a pro-miscuous glycosyltransferase

“…2A). Our previous work demonstrated that such I-Tags generate strong signals in massspectrometry that dominate the analyte ionization and can be employed for yield estimation in biotransformations 48,55,56 . To assess the scope of the glucose polymerization activity, we chemically synthesized the novel 4-(1-methyl-3-methyleneimidazolium) benzyl β-glucoside ITag-Glc-2 (2) ( Fig.…”

Rapid and mild silylation of β‐amino alcohols at room temperature mediated by N‐methylimidazole for enhanced detectability by gas chromatography/electron ionization mass spectrometry

“…Therefore, their detection (either direct or via derivatization) in a matrix may signal the underlying presence of one of these substances [16][17][18] and in addition provide critical chemical forensics information. The panel of β-aminoethyl alcohols (10)(11)(12)(13)(14)(15)(16)(17)(18)(19) chosen for our studies is provided in Fig. 3.…”

“…A second attribute is that the success of PDMS installation in our analytes by this method would strongly support the eventual success of the protocol in the installation of less sterically demanding silyl groups such as TMS and triethylsilyl (TES), as well as other bulky groups such as the tert-butyldimethylsilyl (TBDMS) moiety. [19,20] EXPERIMENTAL Derivatization of the β-aminoethyl alcohols Stock solutions were prepared by dissolving the β-aminoethyl alcohol (100 μL) in 1.5 mL anhydrous methylene chloride. For the derivatization, 100 μL of each β-aminoethyl alcohol stock solution was placed in a 2 mL glass autosampler vial and treated sequentially with the nitrogenous base (pyridine or NMI, 50 μL) followed by chloro(dimethyl)phenylsilane (20 μL).…”

Title Pages

“…Oligosaccharide synthesis may now be performed with S-benzimidazolyl glycosides that may be activated under a variety of conditions 47 , or via an ionic-liquid-supported 'catch-and-release' strategy [ICROS] 48 . Also note Danishefsky′s new peptide ligation 49 , and a new medium for peptide coupling 50 .…”