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Trehalulose

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Not to be confused with Trehalose.
Trehalulose
Names
IUPAC name 1-O-α-D-Glucopyranosyl-D-fructose
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.051.967 Edit this at Wikidata
EC Number
  • 257-183-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: NMELTECMHKKXLF-DGQJZECASA-N
SMILES
  • C(C1C(C(C(C(O1)OCC(=O)C(C(C(CO)O)O)O)O)O)O)O
Properties
Chemical formula C12H22O11
Molar mass 342.297 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. It makes up 50% of sugars in the honeydew of silverleaf whiteflies and is synthesised from sucrose by some bacteria, such as Protaminombacter rubrum. Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.

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. This more stable bond also means that it cannot be utilised by Streptococcus mutans, and it is therefore non-cariogenic.

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 and 0.7.

It has a specific rotation of [ α ] D 20 = + 50 {\displaystyle _{D}^{20}=+50} °.

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. In 2021 the same researchers discovered that the bees convert all sucrose from nectar into trehalulose.

References

  1. ^ 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.{{cite book}}: CS1 maint: location missing publisher (link) 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. ^ 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, Shigeharu et 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.
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