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Chemical Compound Review:

Trehalulose (3S,4R,5R)-3,4,5,6- tetrahydroxy-1-[(2S,3R...

Synonyms: SureCN165502, AC1Q5HKD, AR-1C5059, AR-1C5060, AC1L4QP9, ...

Ooshima, T. et al., Zhang, D. et al., Thompson, J. et al., Cheetham, P.S., Wu, L. et al., et al.

Thompson, Robrish, Pikis, Brust, Lichtenthaler,

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Disease relevance of Trehalulose

Isomaltulose synthase from Klebsiella sp. LX3 (PalI, EC 5.4.99.11) catalyzes the isomerization of sucrose to produce isomaltulose (alpha-D-glucosylpyranosyl-1,6-D-fructofuranose) and trehalulose (alpha-D-glucosylpyranosyl-1,1-d-fructofuranose) [1].
Trehalulose does not induce dental caries in rats infected with mutans streptococci [2].
Streptococcus mutans MT8148R and Streptococcus sobrinus 6715 fermented the syrup which resulted in acid production, while both strains were found not to utilize trehalulose [2].
Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45 [3].

High impact information on Trehalulose

Thirdly, it is reaction-non-selective, forming simultaneously isomaltulose and a second hitherto uncharacterized alpha-(1----1)-linked disaccharide (trehalulose), by hydrolysis of sucrose followed by reaction of glucose with the C-6 and C-1 positions of the fructofuranose respectively [4].
Not only sucrose but the five isomeric alpha-D-glucosyl-D-fructoses trehalulose, turanose, maltulose, leucrose, and palatinose are utilized by Klebsiella pneumoniae as energy sources for growth, thereby undergoing phosphorylation by a phosphoenolpyruvate-dependent phosphotransferase system uniformly at 0-6 of the glucosyl moiety [5].
The effects of trehalulose, a structural isomer of sucrose, and a syrup (TP syrup) rich in trehalulose and palatinose on caries development were examined in specific pathogen-free Sprague-Dawley rats [2].
Although trehalulose induced no significant dental caries in specific pathogen-free rats infected with either MT8148R or 6715, TP syrup was found to induce significant but low dental caries [2].

Associations of Trehalulose with other chemical compounds

In contrast, UQ14S SI showed optimal activity at pH 6 and 35 degrees C and produced a lower ratio of isomaltulose to trehalulose (<8:1) across its pH and temperature ranges for activity [6].

References

Isomaltulose synthase (PalI) of Klebsiella sp. LX3. Crystal structure and implication of mechanism. Zhang, D., Li, N., Lok, S.M., Zhang, L.H., Swaminathan, K. J. Biol. Chem. (2003) [Pubmed]
Trehalulose does not induce dental caries in rats infected with mutans streptococci. Ooshima, T., Izumitani, A., Minami, T., Fujiwara, T., Nakajima, Y., Hamada, S. Caries Res. (1991) [Pubmed]
Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45. Ravaud, S., Watzlawick, H., Haser, R., Mattes, R., Aghajari, N. Acta Crystallograph. Sect. F Struct. Biol. Cryst. Commun. (2005) [Pubmed]
The extraction and mechanism of a novel isomaltulose-synthesizing enzyme from Erwinia rhapontici. Cheetham, P.S. Biochem. J. (1984) [Pubmed]
Phosphorylation and metabolism of sucrose and its five linkage-isomeric alpha-D-glucosyl-D-fructoses by Klebsiella pneumoniae. Thompson, J., Robrish, S.A., Pikis, A., Brust, A., Lichtenthaler, F.W. Carbohydr. Res. (2001) [Pubmed]
Characterization of the highly efficient sucrose isomerase from Pantoea dispersa UQ68J and cloning of the sucrose isomerase gene. Wu, L., Birch, R.G. Appl. Environ. Microbiol. (2005) [Pubmed]

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