Trehalulose
Vorlage:Distinguish Vorlage:Chembox 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.[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]
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References
- ↑ a b c Wolfgang Gerhartz (Hrsg.): Ullmann's encyclopedia of industrial chemistry / Vol. A. Alphabetically arranged articles. 25, Starch and other polysaccharides to surfactants. 5., completely rev Auflage. VCH Verl.-Ges, Weinheim 1994, ISBN 3-527-20125-4, S. 426–427 (worldcat.org).
- ↑ Michael E. Salvucci, Gregory R. Wolfe, Donald L. Hendrix: Effect of sucrose concentration on carbohydrate metabolism in Bemisia argentifolii: Biochemical mechanism and physiological role for trehalulose synthesis in the silverleaf whitefly. In: Journal of Insect Physiology. 43. Jahrgang, Nr. 5, 1. Mai 1997, ISSN 0022-1910, S. 457–464, doi:10.1016/S0022-1910(96)00124-2 (englisch, sciencedirect.com).
- ↑ , Collins, P. M.,: Dictionary of carbohydrates with CD-ROM. 2nd ed Auflage. Boca Raton, ISBN 0-8493-7765-X, S. 538 (worldcat.org).
- ↑ Dénes Hamerli, Robert G. Birch: Transgenic expression of trehalulose synthase results in high concentrations of the sucrose isomer trehalulose in mature stems of field-grown sugarcane. In: Plant Biotechnology Journal. 9. Jahrgang, Nr. 1, 2011, ISSN 1467-7652, S. 32–37, doi:10.1111/j.1467-7652.2010.00528.x (englisch, wiley.com).
- ↑ Ken'ichiro Tsuyuki, Toshiaki Sugitani, Yukie Miyata, Tadishi Ebashi, Yoshikazu Nakajima: Isolation and characterization of isomaltulose- and trehalulose-producing bacteria from Thailand soil. In: The Journal of General and Applied Microbiology. 38. Jahrgang, Nr. 5, 1992, ISSN 1349-8037, S. 483–490, doi:10.2323/jgam.38.483 (doi.org).
- ↑ a b c Kurt Rosenplenter, Prof Dr Gert-Wolfhard von Rymon Lipinski, Prof Dr Ulrich Nöhle: Handbuch Süßungsmittel. Behr's Verlag DE, 2007, ISBN 978-3-89947-947-8, S. 258 (google.de).
- ↑ T. Ooshima, A. Izumitani, T. Minami, T. Fujiwara, Y. Nakajima, S. Hamada: Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci. In: Caries Research. 25. Jahrgang, Nr. 4, 1991, ISSN 0008-6568, S. 277–282, doi:10.1159/000261376, PMID 1913765 (englisch, karger.com).
- ↑ Vorlage:Cite patent
- ↑ Stéphanie Ravaud, Hildegard Watzlawick, Richard Haser, Ralf Mattes, Nushin Aghajari: Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45. In: Acta Crystallographica Section F Structural Biology and Crystallization Communications. 61. Jahrgang, Nr. 1, 1. Januar 2005, ISSN 1744-3091, S. 100–103, doi:10.1107/S1744309104030623, PMID 16508103, PMC 1952383 (freier Volltext) – (iucr.org).