Trehalose

Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate. Mycobacterium tuberculosis antigen 85 mycolyl transferases catalyze transfer of the fatty acid mycolate from one trehalose monomycolate to another, resulting in trehalose dimycolate and free trehalose, thus helping to build the bacterial cell wall. Trehalose 6,6' dimycolate (TDM) or cord factor in the ability of MTB to persist in such lesions without producing inflammation. TDM is unique in that it has three distinct sets of biologic activities depending on its physical conformation. As a single molecule, TDM stimulates macrophage C-type lectin receptors including Mincle. TDM can also form three crystal like structures, cylindrical micelles, intercalated bilayer and monolayer, that have distinct non receptor driven activities that depend on modulation of interactions with water. In the monolayer form, TDM is highly toxic and destroys cells in minutes upon contact

Type : Natural

Chemical_Nomenclature : (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol

Canonical SMILES : C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O

InChI : InChI=1S\/C12H22O11\/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12\/h3-20H,1-2H2\/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-\/m1\/s1

InChIKey : HDTRYLNUVZCQOY-LIZSDCNHSA-N

Other name(s) : D-Trehalose || Alpha,alpha-trehalose || Mycose || Ergot sugar

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