Trehalose, a non-reducing disaccharide composed of two glucose units, is broadly used in the food, cosmetics, biotech, and pharmaceutical industries due to its exceptional biopreservation properties. In addition, due to its autophagic induction properties, trehalose has recently gained traction as a potential therapeutic due to its ability to mitigate disease burden in animal models of metabolic disease and neurodegeneration. However, trehalose can be efficiently broken down by the enzyme trehalase, which allows microorganisms to use trehalose as a food source and potentially contaminate trehalose-containing products. Furthermore, humans possess trehalase in the kidneys and intestinal tract, which could degrade and ultimately limit the effectiveness of trehalose when administered as a therapeutic. 5-Deoxy-5-thio sugars have previously been shown to be resistant to glycosidase-catalyzed hydrolysis, leading us to hypothesize that 5-deoxy-5-thio-D-trehalose may serve as a trehalase-resistant surrogate for trehalose that could be applied in situations where trehalose breakdown is a concern. Here, we report the one-step chemoenzymatic synthesis and conformational analysis of 5-deoxy-5-thio-D-trehalose, as well as its evaluation in trehalase degradation assays.<br/> <br/>

Chemoenzymatic synthesis and evaluation of 5-deoxy-thio-D-trehalose as a trehalase-resistant trehalose surrogate

255th National Meeting (2018)

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