2thioDglucose

2-thio-D-glucose is a non-natural thiosugar that serves as an analog of D-glucose. In this compound, a sulfur atom is incorporated into the sugar framework at the position corresponding to carbon 2, yielding a thio-substituted hexose. The molecule is typically described as retaining the overall D-configuration of glucose, and it may exist as stereoisomeric forms at the anomeric center, producing α- and β-anomers.

Synthesis and structure in brief involve introducing a sulfur-containing group at the 2-position of the sugar skeleton, often through displacement or substitution reactions on a protected glucose derivative, followed by deprotection. The resulting thio analog can be prepared in several isomeric forms depending on the reaction conditions and protecting-group strategy.

Chemical properties of 2-thio-D-glucose reflect the presence of sulfur, which can alter reactivity and intermolecular interactions relative to the parent sugar. The thiolated center can influence ring conformation and hydrogen-bonding patterns, and sulfur may participate in unique interactions such as disulfide formation in appropriate environments. The compound remains highly polar due to multiple hydroxy groups, supporting aqueous solubility, while the sulfur atom can affect lipophilicity and binding properties.

Applications of 2-thio-D-glucose are primarily in biochemical and medicinal chemistry research. It is used as a substrate analog or probe to study enzyme specificity, substrate recognition, and binding interactions in carbohydrate-processing systems. It is not a common metabolite in biology and is typically accessed through targeted synthetic routes for research purposes.