Carbohydrates are essential molecules for life as they are involved in various crucial biological processes, and they feature in drugs and vaccines. Thus, there is a clear need for the comprehensive study of carbohydrates and their structure-activity relationships. However, when compared to the other two main biopolymers, proteins and polynucleotides (DNA and RNA), carbohydrates require both stereo- and regio-chemical control in their synthesis. In order to aid in this, several chemical technologies have been developed for the synthesis of oligosaccharides in an automated and programmable manner. These methods still require access to monosaccharide building blocks which can constitute a majority of the synthetic effort.<br/>Herein we will present the use of the MIDA boronate-based purification tag which has shown to have unusual binding affinities for silica when using different eluent systems . The use of this purification tag to expedite monosaccharide synthesis by simplifying their purification will be described thus enabling more facile access to these building blocks. The compatibility of the MIDA boronate-based tag with common protection and deprotection strategies will also be shown. The tagged building blocks have also been successfully used in glycosylation reactions.

Exploiting MIDA boronates for access to monosaccharide building blocks

ACS Fall 2021

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