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Cryoprotection with L ‐ and meso ‐Trehalose: Stereochemical Implications
Author(s) -
Seo SeungKee,
McClintock Michael L.,
Wei Alexander
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200600322
Subject(s) - trehalose , cryoprotectant , differential scanning calorimetry , chemistry , yeast , carbohydrate , stereochemistry , biochemistry , cryopreservation , biology , thermodynamics , embryo , physics , microbiology and biotechnology
Two unnatural stereoisomers of α,α‐trehalose ( L ‐ and meso ‐trehalose) were synthesized and evaluated as cryoprotectants in order 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 L ‐trehalose were equally effective in maintaining high rates of cell survival, thus 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.