Two unnatural stereoisomers of α,α-trehalose (L-and meso-trehalose) were synthesized and evaluated as cryoprotectants, to determine the functional consequences of relative or absolute stereochemistry on their physicochemical properties. Adherent yeast cell cultures were frozen in 10% solutions of D-, L-, and meso-trehalose for periods of 7−28 days, then evaluated by a MTT viability assay. D-and Ltrehalose were equally effective in maintaining high rates of cell survival, demonstrating the absence of chiral discrimination at the carbohydrate-lipid interface, whereas meso-trehalose was inferior in cryoprotection efficacy. Differential scanning calorimetry revealed a difference in the glass transition temperatures (T g ) of D-and meso-trehalose of nearly 75 °C. This can be attributed to differences in conformational behavior, as portrayed by torsional energy maps for rotation about the glycosidic bonds of D-and meso-trehalose. We conclude that the biostabilizing properties of α,α-trehalose depend on relative stereochemical factors, but are independent of absolute stereochemical configuration.
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