Common NameAlpha,alpha-trehalose
DescriptionTrehalose, 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, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID:12105274 ; PMID:25479689 ) (krishikosh.egranth.ac.in/bitstream/1/84382/1/88571%20P-1257.pdf).
Structure
Molecular FormulaC12H22O11
Average Mass342.29650
Monoisotopic Mass342.11621
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
Traditional NameTrehalose
CAS Registry Number99-20-7
SMILESOC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=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
InChI KeyHDTRYLNUVZCQOY-LIZSDCNHSA-N
CHEBI IDCHEBI:16551
HMDB IDHMDB0000975
Pathways
NameSMPDB/PathBank
Trehalose Degradation
StateNot Available
Water Solubility5.92e+02 g/l
logP-2.98
logS0.24
pKa (Strongest Acidic)11.91
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count11
Hydrogen Donor Count8
Polar Surface Area189.53 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity68.34 m³·mol⁻¹
Polarizability31.20

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