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HEXOSE DERIVATIVES, PREPARATION AND USES THEREOF
EP3116886
A compound of formula I : or a salt thereof, wherein: R1 is -OC(H) (X) (CH2)nC(=O)OH; R2 is -OH, -N3, or -N (H) C (=O) CH3; or R1 and R2 together with the carbon atoms to which they are attached form R3 is -H, -CH3, -CH2C(=O)OH, or -CH2OH; X is -H, -CH3, -CH2OH, or CH2C(=O)OH; and n is 0 or 1.
Low molecular weight organic compounds termed compatible solutes have been identified in the cytoplasm of many halophilic or halotolerant organisms which counterbalance the osmotic pressure of the external medium and which promote correct protein folding, inhibit protein aggregation, and prevent heat-induced denaturation (Faria 2008, Faria 2013). Compatible solutes are therefore industrially useful, for example, for stabilizing proteins in pharmaceutical and cosmetic formulations (Luley-Goedl 2011, Lentzen 2006). Compatible solutes are usually amino acids, carbohydrates, polyols, betaines and ectoines. Trehalose, glycerol, glycine- betaine and ectoine are typical compatible solutes of mesophiles. The discovery of extreme thermophilic and hyperthermophilic microorganisms led to the discovery of additional compatible solutes, such as mannosylglycerate (MG) and dimyo-inositol-1, 3' -phosphate (Faria 2008). Compounds structurally related to MG, namely (2S) -2- (1-O-oc-D- Mannopyranosyl) propionate (ML), 2- ( 1-O-a-Dmannopyranosyl) acetate (MGlyc) , 1-0- (2-glyceryl) -a-D-mannopyranoside (MGOH) , have been synthesized and tested for their ability to stabilize model proteins against thermal stress. (Faria 2008). New compounds for the stabilization of biological materials are needed.