Carbohydrate-based low molecular weight gelators (LMWGs) are important compounds that exhibit many potential applications in various fields, such as effective drug delivery carriers in biomedical research.  In previous studies, our group has demonstrated success in designing and synthesizing LMWGs using monosaccharides such as glucose and glucosamine. In order to understand the structural and gelation properties and obtain more effective LMWGs, in this study we synthesized a series of para-chlorobenzylidene acetal protected D-glucosamine amide derivatives. These compounds contain additional halogen substituents and can allow us to examine the effects of halogen bonding on molecular self-assembly and gelation properties. Eight amide derivatives were prepared from the 4,6-O-(p-chlorobenzylidene) acetal protected D-glucosamine headgroup with the intent of optimizing its ability to form effective LMWGs. Following the synthesis of each derivative, the resulting compound’s self-assembling properties were assessed in multiple organic solvents and aqueous solutions. Several of the D-glucosamine derivatives rendered remarkably stable gels in aqueous solutions with low minimum gelation concentrations (0.5 mg/mL, 1.12 mM). The synthesis and characterization of these D-glucosamine based compounds and their effectiveness as LMWGs are reported.<br/>

Design and synthesis of molecular gelators derived from 4,6-O-(p-chlorobenzylidene)-acetal protected D-glucosamine

2019 Spring National Meeting

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