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Chemical Report for: 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
Other name(s) D-Trehalose ; Alpha,alpha-trehalose ; Mycose ; Ergot sugar

Families | Trehalose ligand of proteins in family: A85-Mycolyl-transferase
Stucture | 1 structure: 1F0P: Mycobacterium tuberculosis Antigen 85B with trehalose
Protein | myctu-a85a, myctu-a85b, myctu-a85c

Search PubMed for references concerning: Trehalose
    Title: Cord factor as an invisibility cloak? A hypothesis for asymptomatic TB persistence
    Hunter RL, Hwang SA, Jagannath C, Actor JK
    Ref: Tuberculosis (Edinb), 101S:S2, 2016 : PubMed


    Title: An interfacial mechanism and a class of inhibitors inferred from two crystal structures of the Mycobacterium tuberculosis 30 kDa major secretory protein (Antigen 85B), a mycolyl transferase.
    Anderson DH, Harth G, Horwitz MA, Eisenberg D
    Ref: Journal of Molecular Biology, 307:671", 2001 : PubMed


    Title: Crystal structure of the secreted form of antigen 85C reveals potential targets for mycobacterial drugs and vaccines
    Ronning DR, Klabunde T, Besra GS, Vissa VD, Belisle JT, Sacchettini JC
    Ref: Nat Struct Biol, 7:141, 2000 : PubMed


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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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