Trehalulose

Last updated
Trehalulose
Trehalulose structure.png
Names
IUPAC name
1-O-α-D-Glucopyranosyl-D-fructose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.051.967 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 257-183-7
KEGG
PubChem CID
UNII
  • InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h4,6-15,17-21H,1-3H2/t4-,6-,7-,8-,9-,10+,11-,12+/m1/s1 Yes check.svgY
    Key: NMELTECMHKKXLF-DGQJZECASA-N
  • C(C1C(C(C(C(O1)OCC(=O)C(C(C(CO)O)O)O)O)O)O)O
Properties
C12H22O11
Molar mass 342.297 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey. [1] It makes up 50% of sugars in the honeydew of silverleaf whiteflies [2] [3] and is synthesised from sucrose by some bacteria, [4] [5] such as Protaminombacter rubrum. [6] [1] Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar. [6]

Contents

Physiology

Because the fructose and glucose molecules are linked by a 1,1 glycosidic bond, which is more stable than the 1,2 glycosidic bond in sucrose, it is broken down more slowly than sucrose in the small intestine, giving it a lower glycemic index. [6] This more stable bond also means that it cannot be utilised by Streptococcus mutans , and it is therefore non-cariogenic. [7]

Properties

Unlike isomaltulose, trehalulose strongly resists crystallisation, and forms an amorphous solid when dried. Its sweetness relative to sucrose has been estimated as between 0.4 [8] and 0.7. [9]

It has a specific rotation of °. [1]

Honey from stingless bees

In 2020 researchers at the University of Queensland found that some species of stingless bee in Australia, Malaysia, and Brazil produce honey containing between 13% and 44% trehalulose rather than the usual glucose and fructose. The university's findings supported the long-standing claims of Indigenous Australian people that native honey is beneficial for human health. [10] [11] In 2021 the same researchers discovered that the bees convert all sucrose from nectar into trehalulose. [12]

Related Research Articles

Biochemistry Study of chemical processes in living organisms

Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and metabolism. Over the last decades of the 20th century, biochemistry has become successful at explaining living processes through these three disciplines. Almost all areas of the life sciences are being uncovered and developed through biochemical methodology and research. Biochemistry focuses on understanding the chemical basis which allows biological molecules to give rise to the processes that occur within living cells and between cells, in turn relating greatly to the understanding of tissues and organs, as well as organism structure and function. Biochemistry is closely related to molecular biology, which is the study of the molecular mechanisms of biological phenomena.

Carbohydrate Organic compound that consists only of carbon, hydrogen, and oxygen

A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula Cm(H2O)n (where m may or may not be different from n). However, not all carbohydrates conform to this precise stoichiometric definition (e.g., uronic acids, deoxy-sugars such as fucose), nor are all chemicals that do conform to this definition automatically classified as carbohydrates (e.g. formaldehyde and acetic acid).

Disaccharide Complex sugar

A disaccharide is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lactose, and maltose.

Glucose Simple form of sugar

Glucose is a simple sugar with the molecular formula ‹See Tfd›C6H12O6. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

Sugar Generic name for sweet-tasting, soluble carbohydrates

Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double sugars, are molecules made of two monosaccharides joined by a glycosidic bond. Common examples are sucrose, lactose, and maltose. Table sugar, granulated sugar, and regular sugar refer to sucrose, a disaccharide composed of glucose and fructose. In the body, compound sugars are hydrolysed into simple sugars.

Fructose Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into blood during digestion. Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847. The name "fructose" was coined in 1857 by the English chemist William Allen Miller. Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars. Fructose is found in honey, tree and vine fruits, flowers, berries, and most root vegetables.

Sucrose Disaccharide composing of glucose and fructose

Sucrose is a type of sugar made up of one molecule of glucose and one molecule of fructose joined together. It is a disaccharide, a molecule composed of two monosaccharides: glucose and fructose. Sucrose is produced naturally in plants, from which white sugar is refined and crystalized. It has the molecular formula C
12
H
22
O
11
.

Benedict's reagent is a chemical reagent and complex mixture of sodium carbonate, sodium citrate, and copper(II) sulfate pentahydrate. It is often used in place of Fehling's solution to detect the presence of reducing sugars. The presence of other reducing substances also gives a positive result. Such tests that use this reagent are called the Benedict's tests. A positive test with Benedict's reagent is shown by a color change from clear blue to brick-red with a precipitate.

Maltose Chemical compound

Maltose, also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When alpha-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.

Xylitol Synthetic sweetener

Xylitol is a chemical compound with the formula C
5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is soluble in water. It can be classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on], "wood", with the suffix -itol used to denote sugar alcohols.

Glycoside Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

Reducing sugar

A reducing sugar is any sugar that is capable of acting as a reducing agent. In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid.

Trehalose Chemical compound

Trehalose is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.

<i>Streptococcus mutans</i> Species of bacterium

Streptococcus mutans is a facultatively anaerobic, gram-positive coccus commonly found in the human oral cavity and is a significant contributor to tooth decay. It is part of the "streptococci", an informal general name for all species in the genus Streptococcus. The microbe was first described by James Kilian Clarke in 1924.

Fructan

A fructan is a polymer of fructose molecules. Fructans with a short chain length are known as fructooligosaccharides. Fructans can be found in over 12% of the angiosperms including both monocots and dicots such as agave, artichokes, asparagus, leeks, garlic, onions, yacón, jícama, barley and wheat.

Isomaltulose Chemical compound

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. The glucose and fructose are linked by an alpha-1,6-glycosidic bond. Isomaltulose is present in honey and sugarcane extracts. It tastes similar to sucrose with half the sweetness. Isomaltulose, also known by the trade name Palatinose, is manufactured by enzymatic rearrangement (isomerization) of sucrose from beet sugar. The enzyme and its source were discovered in Germany in 1950, and since then its physiological role and physical properties have been studied extensively. Isomaltulose has been used as an alternative to sugar in foods in Japan since 1985, in the EU since 2005, in the US since 2006, and in Australia and New Zealand since 2007, besides other countries worldwide. Analytical methods for characterization and assay of commercial isomaltulose are laid down, for example, in the Food Chemicals Codex. Its physical properties closely resemble those of sucrose, making it easy to use in existing recipes and processes.

Glucansucrase

Glucansucrase is an enzyme in the glycoside hydrolase family GH70 used by lactic acid bacteria to split sucrose and use resulting glucose molecules to build long, sticky biofilm chains. These extracellular homopolysaccharides are called α-glucan polymers.

Isomaltooligosaccharide (IMO) is a mixture of short-chain carbohydrates which has a digestion-resistant property. IMO is found naturally in some foods, as well as being manufactured commercially. The raw material used for manufacturing IMO is starch, which is enzymatically converted into a mixture of isomaltooligosaccharides.

Kestose Sugar from fructooligosaccharide group

Kestose is a class of sugars that belongs to a group of fructooligosaccharides.

References

  1. 1 2 3 Wolfgang Gerhartz, ed. (1994). Ullmann's encyclopedia of industrial chemistry / Vol. A. Alphabetically arranged articles. 25, Starch and other polysaccharides to surfactants (5., completely rev ed.). Weinheim: VCH Verl.-Ges. pp. 426–427. ISBN   3-527-20125-4. OCLC   311987978.
  2. Salvucci, Michael E.; Wolfe, Gregory R.; Hendrix, Donald L. (1997-05-01). "Effect of sucrose concentration on carbohydrate metabolism in Bemisia argentifolii: Biochemical mechanism and physiological role for trehalulose synthesis in the silverleaf whitefly". Journal of Insect Physiology. 43 (5): 457–464. doi:10.1016/S0022-1910(96)00124-2. ISSN   0022-1910.
  3. Dictionary of carbohydrates with CD-ROM. Collins, P. M. (2nd ed.). Boca Raton. 29 November 2005. p. 538. ISBN   0-8493-7765-X. OCLC   70262506.CS1 maint: others (link)
  4. Hamerli, Dénes; Birch, Robert G. (2011). "Transgenic expression of trehalulose synthase results in high concentrations of the sucrose isomer trehalulose in mature stems of field-grown sugarcane". Plant Biotechnology Journal. 9 (1): 32–37. doi: 10.1111/j.1467-7652.2010.00528.x . ISSN   1467-7652. PMID   20492546.
  5. Tsuyuki, Ken'ichiro; Sugitani, Toshiaki; Miyata, Yukie; Ebashi, Tadishi; Nakajima, Yoshikazu (1992). "Isolation and characterization of isomaltulose- and trehalulose-producing bacteria from Thailand soil". The Journal of General and Applied Microbiology. 38 (5): 483–490. doi: 10.2323/jgam.38.483 . ISSN   1349-8037.
  6. 1 2 3 Rosenplenter, Kurt; Lipinski, Prof Dr Gert-Wolfhard von Rymon; Nöhle, Prof Dr Ulrich (2007-01-01). Handbuch Süßungsmittel (in German). Behr's Verlag DE. p. 258. ISBN   978-3-89947-947-8.
  7. Ooshima, T.; Izumitani, A.; Minami, T.; Fujiwara, T.; Nakajima, Y.; Hamada, S. (1991). "Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci". Caries Research. 25 (4): 277–282. doi:10.1159/000261376. ISSN   0008-6568. PMID   1913765.
  8. EP 0794259,Nishimoto, Tomoyuki; Chaen, Hiroto& Fukuda, Shigeharuet al.,"Process for producing a saccharide composition containing trehalulose",published 1997-09-10, assigned to Hayashibara Seibutsu Kagaku Kenkyujo KK
  9. Ravaud, Stéphanie; Watzlawick, Hildegard; Haser, Richard; Mattes, Ralf; Aghajari, Nushin (2005-01-01). "Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45". Acta Crystallographica Section F. 61 (1): 100–103. doi:10.1107/S1744309104030623. ISSN   1744-3091. PMC   1952383 . PMID   16508103.
  10. Layt, Stuart (2020-07-23). "Scientists say native stingless bee honey hits the sweet spot". Brisbane Times. Retrieved 2020-07-27.
  11. Fletcher, Mary T.; Hungerford, Natasha L.; Webber, Dennis; Carpinelli de Jesus, Matheus; Zhang, Jiali; Stone, Isobella S. J.; Blanchfield, Joanne T.; Zawawi, Norhasnida (2020-07-22). "Stingless bee honey, a novel source of trehalulose: a biologically active disaccharide with health benefits". Scientific Reports. 10 (1): 12128. Bibcode:2020NatSR..1012128F. doi: 10.1038/s41598-020-68940-0 . ISSN   2045-2322. PMC   7376065 . PMID   32699353.
  12. "Native bees make a healthy honey no others make, and now we know how". ABC News. 27 August 2021.