D(+)-Trehalose dihydrate: Properties, Synthesis, Function and Uses

D-(+)-Trehalose is a disaccharide composed of two α-glucose units. It is used as a cryoprotectant in a variety of cell freezing media.

Chemical Properties

Trehalose is a nonreducing sugar formed from two glucose units joined by a 1–1 alpha bond, giving it the name α-D-gluco­pyranosyl-(1→1)-α-D-gluco­pyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore is stable in solution at high temperatures, even under acidic conditions. The bonding keeps nonreducing sugars in closed-ring form, such that the aldehyde or ketone end groups do not bind to the lysine or arginine residues of proteins (a process called glycation). Trehalose is less soluble than sucrose, except at high temperatures (>80 °C). Trehalose forms a rhomboid crystal as the dihydrate, and has 90% of the calorific content of sucrose in that form. Anhydrous forms of trehalose readily regain moisture to form the dihydrate.

D-(+)-Trehalose Synthesis

At least three biological pathways support trehalose biosynthesis. An industrial process can derive trehalose from corn starch.

D-(+)-Trehalose Function

D-(+)-Trehalose has high water retention capabilities and can be used to form gels or prevent desiccation. Derivatives of trehalose exhibit anticancer, anti-metastatic, and neuromodulatory activities; they may also induce autophagy and modulate activity of toll-like receptors (TLRs).

D-(+)-Trehalose Uses

D-(+)-Trehalose can be used as a carbohydrate reserve in certain cell cultures to tide over environmental stresses. It can also be used in biopharmaceutical monoclonal antibody formulations and as a protein stabilizer.

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