Trehalose

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Structural formula
Structure of trehalose
General
Surname Trehalose
other names
  • 1-α-glucopyranosyl-1-α-glucopyranoside
  • 2- (Hydroxymethyl) -6- [3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydropyran-2-yl] oxy-tetrahydropyran-3,4,5-triol
  • Mycosis
Molecular formula C 12 H 22 O 11
Brief description

colorless solid

External identifiers / databases
CAS number
  • 99-20-7 (α, α- D -rehalose)
  • 585-91-1 (α, β- D -rehalose)
  • 6138-23-4 (α, β- D- trehalose dihydrate)
  • 499-23-0 (β, β- D -rehalose)
  • 25018-27-3 (trehalose octaacetate)
EC number 202-739-6
ECHA InfoCard 100.002.490
PubChem 7427
Wikidata Q421773
properties
Molar mass 342.30 g · mol -1
Physical state

firmly

Melting point
  • 214–216 ° C (α, α- D -rehalose)
  • 149 ° C (α, β- D -rehalose)
  • 135–140 ° C (β, β- D -rehalose)
solubility
safety instructions
GHS labeling of hazardous substances

Dihydrate

no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trehalose (also called fungal sugar or mycosis ) is a disaccharide (outdated double sugar), which consists of two α, α'-1,1-glycosidically linked glucose molecules. Hence its systematic name is 1-α-glucopyranosyl-1-α-glucopyranoside, in the short formula: Glc α (1 → 1) α Glc. Since both anomeric carbon atoms are involved in the O-glycosidic bond , trehalose is one of the non-reducing sugars.

Occurrence

Trehalose occurs naturally in various plants and fungi and also in the hemolymph of many insects. It comes in the cocoons of weevil larvae of Larinus maculatus , Larinus nidificans before; these were previously collected and referred to as "Trehala Manna", hence the name Trehal -ose. These cocoons contain about 30–45% trehalose. It is one of the reserve substances in plants . It can be broken down into D- glucose by humans using trehalase located in the small intestine .

Trehalose is essential for bacteria: only through the enrichment of trehalose can they survive stressful situations such as drought without their proteins denaturing. Corynebacteria and mycobacteria also incorporate trehalose as a component of glycolipids in their outermost cell wall layer , where it facilitates the penetration of the host organism in pathological germs.

Function / applications

  • Trehalose is also known as a natural antifreeze . In tardigrades (Tardigrada), the significant increase in the intracellular trehalose concentration leads to cryopreservation . In various tissues, the artificial addition of trehalose in combination with other substances (e.g. DMSO ) leads to cryopreservation .
  • In insects in particular, trehalose is the main reserve sugar, and inhibition of trehalase can lead to death due to hypoglycemia , which is used in insect control.
  • Trehalose is produced industrially from starch. It has about 45% of the sweetness of sugar and is used as a sugar substitute .
  • In the medical field, trehalose - in combination with hyaluronic acid - is used to treat dry eyes . Trehalose protects the cornea and conjunctiva from damage caused by dryness by forming a kind of protective film on the cell surface. Trehalose also has a high water-binding capacity and is therefore a suitable ingredient for a tear substitute.

literature

  • Iturriaga G, Suárez R, Nova-Franco B: Trehalose metabolism: from osmoprotection to signaling . In: Int. J. Mol. Sci . 10, No. 9, September 2009, pp. 3793-3810. doi : 10.3390 / ijms10093793 . PMID 19865519 . PMC 2769160 (free full text).
  • Kurt Rosenplenter, Ulrich Nöhle (ed.): Handbook sweeteners. 2nd edition, Behrs Verlag, ISBN 978-3-89947-262-2 , pp. 242-257, 265-269.

Web links

Commons : Trehalose  - collection of images, videos and audio files

Individual evidence

  1. ↑ a b c Data sheet D - (+) - Trehalose dihydrate from Sigma-Aldrich , accessed on June 16, 2011 ( PDF ).
  2. ↑ a b c d e Entry on trehalose. In: Römpp Online . Georg Thieme Verlag, accessed on December 25, 2014.
  3. ↑ NK Jain, I. Roy: Effect of trehalose on protein structure . In: Protein Sci . 18, No. 1, January 2009, pp. 24-36. doi : 10.1002 / pro.3 . PMID 19177348 . PMC 2708026 (free full text).
  4. ↑ M. Tropis, X. Meniche, A. Wolf et al. a .: The crucial role of trehalose and structurally related oligosaccharides in the biosynthesis and transfer of mycolic acids in Corynebacterineae . In: J. Biol. Chem . 280, No. 28, July 2005, pp. 26573-26585. doi : 10.1074 / jbc.M502104200 . PMID 15901732 .
  5. ^ Y. Neuman: Cryptobiosis: a new theoretical perspective. In: Prog. Biophys. Mol. Biol. 92 (2), 2006, 258-267, doi : 10.1016 / j.pbiomolbio.2005.11.001 .
  6. ↑ E. Katenz et al. a .: Cryopreservation of primary human hepatocytes: the benefit of trehalose as an additional cryoprotective agent. In: Liver Transplantation . 13, 2007, 38-45, doi : 10.1002 / lt.20921 .
  7. ↑ G. Wegener, V. Tschiedel, P. Schlöder, O. Ando: The toxic and lethal effects of the trehalase inhibitor trehazolin in locusts are caused by hypoglycaemia . In: J. Exp. Biol . 206, No. Pt 7, April 2003, pp. 1233-1240. PMID 12604583 .
  8. ↑ Patient information sheet dry eye , Theapharma website, accessed on July 17, 2018