Chemistry:Trehalulose
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| IUPAC name
1-O-α-D-Glucopyranosyl-D-fructose
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| 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]
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 [math]\displaystyle{ [\alpha]_D^{20} = +50 }[/math]°.[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]
References
- ↑ 1.0 1.1 1.2 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. https://www.worldcat.org/oclc/311987978.
- ↑ 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" (in en). Journal of Insect Physiology 43 (5): 457–464. doi:10.1016/S0022-1910(96)00124-2. ISSN 0022-1910. http://www.sciencedirect.com/science/article/pii/S0022191096001242.
- ↑ Dictionary of carbohydrates with CD-ROM. Collins, P. M. (2nd ed.). Boca Raton. 29 November 2005. pp. 538. ISBN 0-8493-7765-X. OCLC 70262506. https://www.worldcat.org/oclc/70262506.
- ↑ 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" (in en). Plant Biotechnology Journal 9 (1): 32–37. doi:10.1111/j.1467-7652.2010.00528.x. ISSN 1467-7652. PMID 20492546.
- ↑ 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.
- ↑ 6.0 6.1 6.2 Rosenplenter, Kurt; Lipinski, Prof Dr Gert-Wolfhard von Rymon; Nöhle, Prof Dr Ulrich (2007-01-01) (in de). Handbuch Süßungsmittel. Behr's Verlag DE. p. 258. ISBN 978-3-89947-947-8. https://books.google.com/books?id=xAG7yyKWEi0C&pg=PA259.
- ↑ 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" (in en). Caries Research 25 (4): 277–282. doi:10.1159/000261376. ISSN 0008-6568. PMID 1913765. https://www.karger.com/Article/FullText/261376.
- ↑ Nishimoto, Tomoyuki; Hiroto Chaen & Shigeharu Fukuda et al., "Process for producing a saccharide composition containing trehalulose", EP patent 0794259, published 1997-09-10
- ↑ 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. PMID 16508103. PMC 1952383. http://scripts.iucr.org/cgi-bin/paper?S1744309104030623.
- ↑ Layt, Stuart (2020-07-23). "Scientists say native stingless bee honey hits the sweet spot" (in en). https://www.brisbanetimes.com.au/national/queensland/scientists-say-native-stingless-bee-honey-hits-the-sweet-spot-20200723-p55eud.html.
- ↑ 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" (in en). Scientific Reports 10 (1): 12128. doi:10.1038/s41598-020-68940-0. ISSN 2045-2322. PMID 32699353. Bibcode: 2020NatSR..1012128F.
- ↑ "Native bees make a healthy honey no others make, and now we know how". ABC News. 27 August 2021. https://www.abc.net.au/news/rural/2021-08-28/native-bees-healthy-honey/100409558.
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