Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci

Ooshima, Takashi; Izumitani, A; Minami, Takahiro; Fujiwara, Taku; Nakajima, Yoshikazu; Hamada, Shigeyuki

doi:10.1159/000261376

Cited by 55 publications

(28 citation statements)

References 7 publications

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“…Enzyme mutants were analyzed by their ability to act on sucrose and the amount of released products. The product composition following 100 mM sucrose conversion was measured after ϳ90% substrate consumption, and concentrations of the individual sugars were determined by high performance anion exchange chromatography (HPLC) 3 with pulse amperometric detection. The samples were separated on a CarboPac PA1 column (Dionex) with 0.22 M NaOH, 0.02 M NaAc at a flow rate of 0.75 ml/min.…”

Section: Methodsmentioning

confidence: 99%

“…Data Collection-Crystals used for the diffraction experiments typically measured 0.8ϫ0.2ϫ0.03 mm 3 and were cryo-protected prior to data collection by rapid soaking (1 min) in mother liquor containing 20% (v/v) glycerol and for MutB⅐deoxynojirimycin, MutB⅐castanospermine, D200A⅐glucose, and E254Q⅐sucrose, the corresponding ligand molecule at the concentration used for co-crystallization or soaking experiments.…”

Section: Volume 282 • Number 38 • September 21 2007mentioning

confidence: 99%

“…1C) (1,2). Moreover, they are acariogenic (3), and their absorption reduces the rate with which monosaccharides and insulin are released into the bloodstream (4) and can thus be applied in diabetic and sports foods and drinks. Considering also that no side effects have been yet reported, these compounds could be ideal sucrose substitutes.…”

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confidence: 99%

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Trehalulose Synthase Native and Carbohydrate Complexed Structures Provide Insights into Sucrose Isomerization

Ravaud

Robert

Watzlawick

et al. 2007

Journal of Biological Chemistry

137

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Various diseases related to the overconsumption of sugar make a growing need for sugar substitutes. Because sucrose is an inexpensive and readily available D-glucose donor, the industrial potential for enzymatic synthesis of the sucrose isomers trehalulose and/or isomaltulose from sucrose is large. The product specificity of sucrose isomerases that catalyze this reaction depends essentially on the possibility for tautomerization of sucrose, which is required for trehalulose formation. For optimal use of the enzyme, targeting controlled synthesis of these functional isomers, it is necessary to minimize the side reactions. This requires an extensive analysis of substrate binding modes and of the specificity-determining sites in the structure. The 1.6 -2.2-Å resolution three-dimensional structures of native and mutant complexes of a trehalulose synthase from Pseudomonas mesoacidophila MX-45 mimic successive states of the enzyme reaction. Combined with mutagenesis studies they give for the first time thorough insights into substrate recognition and processing and reaction specificities of these enzymes. Among the important outcomes of this study is the revelation of an aromatic clamp defined by Phe 256 and Phe 280 playing an essential role in substrate recognition and in controlling the reaction specificity, which is further supported by mutagenesis studies. Furthermore, this study highlights essential residues for binding the glucosyl and fructosyl moieties. The introduction of subtle changes informed by comparative three-dimensional structural data observed within our study can lead to fundamental modifications in the mode of action of sucrose isomerases and hence provide a template for industrial catalysts.

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Section: Methodsmentioning

confidence: 99%

Section: Volume 282 • Number 38 • September 21 2007mentioning

confidence: 99%

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Trehalulose Synthase Native and Carbohydrate Complexed Structures Provide Insights into Sucrose Isomerization

Ravaud

Robert

Watzlawick

et al. 2007

Journal of Biological Chemistry

137

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“…Trehalulose is a white crystalline powder with a melting point of 48 C, which is highly water soluble and more hygroscopic than isomaltulose. 22,36) This non cariogenic sweetener, displaying a sweetening power of 70% of that of sucrose, 2,36) is used especially in foods enriched with sweeteners such as jams, and sweet jellies. Furthermore, it is used as a taste and quality improving agent, and as a stabilizer in food products, pet foods, cosmetics, and pharmaceuticals.…”

Section: )mentioning

confidence: 99%

Structure/Function Relationships of Sucrose Isomerases with Different Product Specificity

et al. 2010

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Sucrose and its substitutes.Sucrose (α D glucopyranosyl 1,2 β D fructofuranoside), called table sugar, is the most common sugar produced and accumulated by plants. 1) Large quantities of the disaccharide accumulate in the edible parts of some plants. 2) Currently, sucrose is used in many agro alimentary products. Nevertheless, though this disaccharide is cheap and easily produced from sugar cane or sugar beets, it is highly caloric. It is well known that the quantity and the frequency of sucrose consumption may induce metabolic and pathologic effects. Indeed, sucrose is efficiently metabolized, thereby influencing the glycaemia of the body and promoting dental caries.3) In mammals, sucrose is rapidly absorbed into the bloodstream in the small intestine and is hydrolysed into glucose and fructose. The ingestion of sucrose raises blood glucose and can cause problems for people suffering from defects in glucose metabolism, such as persons with hypoglycaemia or diabetes. These effects have stimulated the interest in finding other naturally occurring and synthetic sweeteners. Two parameters are critical for defining efficient sucrose substitutes; they should have nutritional qualities and not be harmful to the general health of the individual. 4) Many non or low cariogenic synthetic sugar substitutes are currently available and are found as ingredients in a variety of candies, drinks and diet food, and still novel compounds emerge. 5,6) The main sugar substitutes used to date are aspartame, saccharine, sucralose, and acésulfalme K. No sweetener is a perfect replacement for sucrose, the main limitation being their taste profiles. Moreover, sweeteners are among the most actively discussed additives because of their side effects on health, including dermatological problems, headaches, mood variations, respiratory difficulties, seizures and cancer. 7,8) Five different structural isomers of sucrose composed of glucose and fructose exist with inter glucosidic linkages being α 1,1 (trehalulose), α 1,3 (turanose), α 1,4 (maltulose), α 1,5 (leucrose) and α 1,6 (isomaltulose) as depicted in Fig. 1. These analogues are found in honey, sugar cane and other natural products in very low concentrations. Among these, isomaltulose is the sucrose analogue that has been most extensively studied.9 19) Isomaltulose ( α D glucopyranosyl 1,6 D fructofuranose ) , also known as palatinose, and trehalulose (α D glucopyranosyl 1,1 D fructopyranose) are natural and structural isomers of sucrose that have a sweet taste and very similar physical and organoleptic properties to sucrose. 20 22) Therefore they have been suggested as non cariogenic alternatives to sucrose and are widely used in health products and the food industry as e.g., soft drinks, chewing gums, cakes, candies, chocolate and toothpaste for isomaltulose and food and cosmetic products for trehalulose. 23)Isomaltulose and trehalulose properties and production. Isomaltulose and trehalulose possess sweetening powers of 30% and 70%, respectively, when compared to that of sucrose. 2,10,...

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“…The utilization of sucrose by the oral streptococci, Streptococcus mutans and Streptococcus sobrinus, is a major factor in the etiology of dental caries (38,39). Remarkably, oral streptococci are unable to metabolize the isomers of sucrose (34,40,41). Three of the five ␣-D-glucosyl-D-fructoses (palatinose, trehalulose, and leucrose) are now produced on the industrial scale, and, because they are noncariogenic and ϳ50% as sweet as sucrose, these isomers attract attention as potential substitutes for dietary sucrose (11,12).…”

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confidence: 99%

Genes malh and pagl of Clostridium acetobutylicum ATCC 824 Encode NAD+- and Mn2+-dependent Phospho-α-glucosidase(s)

Thompson

Hess

Pikis

2004

Journal of Biological Chemistry

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The genome of Clostridium acetobutylicum 824 contains two genes encoding NAD ؉ , Mn 2؉ , and dithiothreitol-dependent phospho-␣-glucosidases that can be assigned to family 4 of the glycosylhydrolase superfamily. The two genes, designated malh (maltose 6-phosphate hydrolase) and pagl (phospho-␣-glucosidase), respectively, reside in separate operons that also encode proteins of the phosphoenolpyruvate-dependent:sugar phosphotransferase system. C. acetobutylicum grows on a variety of ␣-linked glucosides, including maltose, methyl-␣-D-glucoside, and the five isomers of sucrose. In the presence of the requisite cofactors, extracts of these cells readily hydrolyzed the chromogenic substrate p-nitrophenyl-␣-D-glucopyranoside 6-phosphate, but whether hydrolysis reflected expression of enzymes encoded by the malh or pagl genes was not discernible by spectrophotometric analysis or polyacrylamide gel electrophoresis. Resolution of this question required the cloning of the malh and pagl genes, and subsequent high expression, purification, and characterization of maltose-6 -phosphate hydrolase (MalH) and phospho-␣-glucosidase (PagL), respectively. MalH and PagL exhibit 50% residue identity, and in solution are tetramers comprising similar sized (ϳ50 kDa) subunits. The two proteins cross-react with polyclonal rabbit antibody against phospho-␣-glucosidase from Fusobacterium mortiferum. Purified MalH and PagL cleaved p-nitrophenyl-␣-D-glucopyranoside 6-phosphate with comparable efficiency, but only MalH catalyzed the hydrolysis of disaccharide 6 -phosphates formed via the phosphoenolpyruvate-dependent:sugar phosphotransferase system. Importantly, analysis of the proteome of C. acetobutylicum 824 by electrospray ionization-mass spectrometry confirmed expression of MalH during growth on many ␣-glucosides tested. Site-directed changes C169S and D170N yielded full-length, but catalytically inactive MalH. Of the two putative operons, our findings suggest that only proteins encoded by the mal operon participate in the dissimilation of maltose and related O-␣-linked glucosides by C. acetobutylicum 824.

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Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci

Cited by 55 publications

References 7 publications

Trehalulose Synthase Native and Carbohydrate Complexed Structures Provide Insights into Sucrose Isomerization

Trehalulose Synthase Native and Carbohydrate Complexed Structures Provide Insights into Sucrose Isomerization

Structure/Function Relationships of Sucrose Isomerases with Different Product Specificity

Genes malh and pagl of Clostridium acetobutylicum ATCC 824 Encode NAD+- and Mn2+-dependent Phospho-α-glucosidase(s)

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