ImageFile = Trehalose.svg
ImageSize = 250px
OtherNames = α-Ｄ-glucopyranosyl α-Ｄ-glucopyranoside(α,α‐Trehalose)
IUPACName = 2-(hydroxymethyl)-6- [3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] oxy-tetrahydropyran-3,4,5-triol
Formula = C12H22O11(anhydride)
Section1 = Chembox Identifiers
CASOther = CAS|99-20-7 (anhydrate)
PubChem = 7427
Section2 = Chembox Properties
MolarMass= 342.296 g/mol (anhydrous crystals)
378.33 g/mol (dihydrate)
Appearance =White crystals
MeltingPt = 203 ℃ (anhydrate)
97 ℃ (dihydrate)
Solubility = 68.9 g in 100 g of water at 20 ºC [ [http://www.iupac.org/publications/pac/2002/pdf/7407x1263.pdf T. Novel functions and applications of trehalose. Pure Appl. Chem. 74(7):1263-1269. 2002.] ]
Section3 = Chembox Structure
Section4 = Chembox Thermochemistry
Section5 = Chembox Pharmacology
Section6 = Chembox Explosive
Section7 = Chembox Hazards
Section8 = Chembox Related
Trehalose, also known as mycose, is a natural alpha-linked
disaccharideformed by an α, α-1, 1-glucoside bond between two α-glucose units. In 1832 Wiggers discovered trehalose in an ergotof rye and in 1859 Berthelot isolated it from trehala manna, a substance made by weevils, and named it trehalose. It can be synthesised by fungi, plants, and invertebrate animals. It is implicated in anhydrobiosis — the ability of plants and animals to withstand prolonged periods of desiccation. It has high water retention capabilities and is used in food and cosmetics. The sugaris thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organellesby effectively splinting them in position. Rehydrationthen allows normal cellular activity to be resumed without the major, lethal damage that would normally follow a dehydration/re-hydration cycle. Trehalose has the added advantage of being an antioxidant. Extracting trehalose used to be a difficult and costly process, but, recently, the Hayashibara company (Okayama, Japan) confirmed an inexpensive extraction technology from starch for mass production. Trehalose is now being used for a broad spectrum of applications.
Trehalose is a disaccharide formed by a 1, 1-glucoside bond between two α-glucose units. Because trehalose is formed by the bonding of two reducing groups, it has no capacity to reduce other compounds.
Also referred to as tremalose.
Trehalose was first isolated from
ergotof rye. Emil Fischer first described the trehalose-hydrolyzing enzymein yeast. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of α-D-glucopyranosyl-(1→1)-α-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 aldehydeor ketoneend-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). Trehalose is broken down by the enzyme trehalaseinto glucose. Trehalose has about 45% the sweetness of sucrose. Trehalose is less soluble than sucrose, except at high temperatures (>80 °C). Trehalose forms a rhomboid crystal as the dihydrate, and has 90% of the calorific content of sucrose in that form. Anhydrous forms of trehalose readily regain moisture to form the dihydrate. Anhydrous forms of trehalose can show interesting physical properties when heat-treated.
Trehalose can be found in nature, animals, plants, and microorganisms. In animals, trehalose is prevalent in shrimp, and also in insects, including grasshoppers, locusts, butterflies, and bees, in which blood-sugar is trehalose. The trehalose is then broken down into glucose by the catabolic enzyme trehalase for use. Trehalose is also present in the nutrition exchange liquid of hornets and their larvae.
In plants, the presence of trehalose is seen in sunflower seeds, selaginella plants, and sea algae. Within the fungus family, it is prevalent in some mushrooms such as
shiitake"(Lentinula edodes)", maitake("Grifola fondosa"), nameko("Pholiota nameko"), and Judas's ear("Auricularia auricula-judae") which can contain 1% to 17% percent of trehalose in dry weight form (thus it is also referred to as mushroom sugar). Trehalose can also be found in such microorganisms as baker's yeastand wine yeast, and it is metabolized by a number of bacteria, including Streptococcus mutans, the common oral bacteria responsible for dental plaque.
tardigrades (water bears) dry out, the glucosein their bodies changes to trehalose when they enter a state called cryptobiosis- a state wherein they appear dead. However, when they receive water, they revive and return to their metabolic state. It is also thought that the reason the larva of sleeping chironomid(polypedihum vanderplanki) and artemia (sea monkeys, brine shrimp) are able to withstand dehydration is because they store trehalose within their cells.
Even within the plant kingdom, selaginella (sometimes called the resurrection plant) which grows in desert and mountainous areas, may be cracked and dried out but will turn green again and revive after a rain, because of the function of trehalose. It is also said that the reason dried
shiitakemushrooms spring back into shape so well in water is because they contain trehalose.
The two prevalent theories as to how trehalose works within the organism in the state of cryptobiosis are the
vitrificationtheory, a state that prevents ice formation, or the water displacement theory, whereby water is replaced by trehalose [cite journal | author=Sola-Penna M, Meyer-Fernandes JR | title=Stabilization against thermal inactivation promoted by sugars on enzyme structure and function: why is trehalose more effective than other sugars? | journal=Archives Of Biochemistry And Biophysics | volume=360 | issue=1 | year=1998 | pages=10–14 | pmid=9826423 | doi=10.1006/abbi.1998.0906] , although it is possible that a combination of the two theories are at work.
The enzyme trehalase, a
glycoside hydrolase, present but not abundant in most people, breaks trehalose into two glucose molecules, which can then be readily absorbed in the gut.
Trehalose is the major carbohydrate energy storage molecule used by insects for flight. One possible reason for this is that the double glycosidic linkage of trehalose, when acted upon by an insect trehalase, releases two molecules of glucose, which is required for the rapid energy requirements of flight. This is double the efficiency of glucose release from the storage polymer starch, for which cleavage of one glycosidic linkage releases only one glucose molecule.
Trehalose was previously being manufactured through an extraction process from cultured yeast, but, since production costs were prohibitive, use was limited to only certain cosmetics and chemicals.
In 1994, Hayashibara, a saccharified starch maker in Okayama prefecture discovered a method of inexpensively mass-producing trehalose from starch. The following year, Hayashibara started marketing trehalose by activating two enzymes, the glucosyltrehalose-producing enzyme that changes the reducing terminal of starch into a trehalose structure, and the trehalose free enzyme that detaches this trehalose structure. As a result, a high-purity trehalose from starch can be mass-produced for a very low price.
Trehalose has been accepted as a novel food ingredient under the GRAS terms in the U.S. and the EU. Trehalose has also found commercial application as a food ingredient. The uses for trehalose span a broad spectrum that cannot be found in other sugars, the primary one being its use in the processing of foods. Trehalose is used in a variety of processed foods such as dinners, western and Japanese confectionery, bread, vegetables side dishes, animal-derived deli foods, pouch-packed foods, frozen foods, and beverages, as well as foods for lunches, eating out, or prepared at home. This use in such a wide range of products is due to the multi-faceted effects of trehalose's properties, such as its inherently mild, sweet flavor; its preservative properties, which maintain the quality of the three main nutrients (carbohydrates, proteins, fats); its powerful water-retention properties, which preserve the texture of foods by protecting them from drying out or freezing; and its ability to suppress bitterness, stringency, harsh flavors, and the stench of raw foods, meats, and packaged foods. These properties, when combined can potentially bring about promising results for broad-spectrum use. However, as it is less-soluble and less-sweet than sucrose, trehalose is seldom used as a direct replacement for conventional
sweeteners, such as sucrose, which is regarded as the "gold standard." Technology for the production of trehalose was developed in Japan, where enzyme-based processes convert wheat and corn syrups to trehalose. It is also used as a protein-stabilizing agent in research. [ T. Arikawa et al / Advanced Drug Delivery Reviews 46 (2001) 307-326 ] It is particularly effective when combined with phosphate ions [U.S. Patent 6,653,062] . Trehalose has also been used in several biopharmaceutical monoclonal antibodyformulations: trastuzumab, marketed as Herceptin by Genentech, and ranibizumab, marketed as Lucentis by Genentech and Novartis.
Cosmetics: Capitalizing on trehalose's moisture-retaining capacity, it is used as a moisturizer in many basic toiletries such as bath oils and hair growth tonics.
Pharmaceuticals: Using trehalose's properties to preserve tissue and protein to full advantage, it is used in organ protection solutions for organ transplants.
Other: Other fields of use for trehalose span a broad spectrum including fabrics that have deodorization qualities, plant activation, antibacterial sheets, and nutrients for larvae.
After trehalose became readily available in mass quantities at a low price, all kinds of research involving trehalose accelerated rapidly. Research is being conducted, especially in the field of medicine, to achieve uses for trehalose in post-surgery adhesion suppressants, dry-eye treatments and the manufacturing of dry blood.
* [http://www.benbest.com/cryonics/vitrify.html#sugars Cryopreservation with Sugars]
* [http://www.iupac.org/publications/pac/2002/pdf/7407x1263.pdf Novel functions and applications of trehalose]
* [http://www.freepatentsonline.com/5484714.html Tremalose]
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Look at other dictionaries:
Trehalose — Tréhalose Tréhalose Tréhalose : (I) : modèle éclaté en 3D ; (II) : formule en chaise Général … Wikipédia en Français
Tréhalose — Tréhalose : (I) : modèle éclaté en 3D ; (II) : formule en chaise Général … Wikipédia en Français
tréhalose — [ trealoz ] n. m. • 1857; de tréhala « galle du chardon » (du turc tigalah) et 1. ose ♦ Biochim. Disaccharide présent dans certains champignons. ● tréhalose nom masculin (de tréhala, galle produite par un insecte) Hydrate de carbone présent dans… … Encyclopédie Universelle
Trehalose — Tre ha*lose , n. (Chem.) Mycose; so called because sometimes obtained from trehala. [1913 Webster] … The Collaborative International Dictionary of English
trehalose — trehalose. См. трегалоза. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) … Молекулярная биология и генетика. Толковый словарь.
Trehalōse — Trehalōse, s. Mykose … Meyers Großes Konversations-Lexikon
Trehalose — Trehalōse, s. Mykose … Kleines Konversations-Lexikon
trehalose — [trē′hə lōs΄, tri häl′ōs΄] n. [< ModL trehala, substance of cocoon of a certain beetle, the orig. source of the sugar (prob. < Pers tīghāl) + OSE1] a disaccharide extracted from yeast, mushrooms, and other fungi … English World dictionary
Trehalose — Strukturformel Allgemeines Name Trehalose Andere Namen … Deutsch Wikipedia
Trehalose — Tre|ha|lo|se [nlat. trehala (türkisch ti̅qa̅lah) = aus Kokons eines in Kleinasien heimischen Käfers Larinus maculatus gewonnene Süßigkeit; ↑ ose (1)], die; , n; Syn.: Mycose: aus Pilzen, Hefe u. a. niederen Pflanzen isolierbares krist.… … Universal-Lexikon