The Preparation, Properties and Structure of the Disaccharide Leucrose

Stodola, Frank H.; Sharpe, E. S.; Koepsell, H. J.

doi:10.1021/ja01592a050

Cited by 98 publications

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“…Leucrose preparations were a crystalline white ma terial with [a]p (c = 10.24 in FLO) of -6.77°C and F = 159-I60°C, thus comparing well with literature data [Stodola et al, 1956: Ruttloff et al, 1964Heeswijk et al, 1978]. Typical analyses of leucrose were 0-0.023% (w/w) glucose, 0.008-0.04% (w/w) fructose, 0-0.04% isomaltulose and no detectable sucrose.…”

Section: Methodssupporting

confidence: 80%

Cariological Assessment of Leucrose [D-Glucopyranosyl-α(1→5)-D-Fructopyranose] as a Sugar Substitute

Ziesenitz¹,

Siebert²,

Imfeld³

1989

Caries Res

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Leucrose [D-glucosyl-α(1→5)-D-fructopyranose] prepared by microbial-enzymatic transglycosidation from sucrose, is the first α(1→5)-linked disaccharide which possesses excellent nutritional properties with regard to metabolic utilization and is well tolerated. The aim of the present work was to assess its cariogenic potential. Yeast invertase was shown to be inhibited by leucrose in a noncompetitive way, while hydrogenated leucrose (leucritol) acted as an activator. Plaque polysaccharide forming glucosyltransferases from Streptococcus cricetus AHT were not influenced by leucrose, but by leucritol. Essentially no acid formation was observed after incubation of leucrose with suspensions of human dental plaque, S. mutans NCTC 10449, Lactobacillus casei LSB 132 and Actinomyces viscosus Ny 1 No. 30. Leucrose was a competitive inhibitor of the acid formation from sucrose by S. mutans NCTC 10449 at neutral pH. Furthermore, leucrose inhibited at neutral pH considerably the uptake of sucrose by S. mutans NCTC 10449. The uptake of fructose and maltose was also inhibited but that of glucose not at all. In Cara rats as the animal model, leucrose was compared to sucrose and to corn starch for its cariogenic potential. In sharp contrast to the group fed with 30% sucrose, caries scores of the 30% leucrose group were not significantly different from the starch group. pH telemetry with an indwelling electrode in man proved leucrose to be ‘safe for teeth’ since plaque pH did not drop below pH 5.7. Leucrose is a novel noncariogenic disaccharide and thus represents a highly promising sugar substitute for caries prevention.

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Section: Methodssupporting

confidence: 80%

Cariological Assessment of Leucrose [D-Glucopyranosyl-α(1→5)-D-Fructopyranose] as a Sugar Substitute

Ziesenitz¹,

Siebert²,

Imfeld³

1989

Caries Res

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“…The addition of 2.5 and 5% mannitol to the food of rats and mice, respectively, for a period of two years showed that mannitol exhibits no carcinogenic properties [219]. The formation of isomaltulose in the fermentation broth of Leuconostoc mesenteroides was first suspected in 1952 [220,221]. The structure was elucidated in 1957 [222].…”

Section: Physiology Tolerance Toxicologymentioning

confidence: 99%

Sugar Alcohols

Schiweck¹,

Bär²,

Vogel³

et al. 2011

Ullmann's Encyclopedia of Industrial Chemistry

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“…This reaction continues until 85-90% of the sucrose is converted to leucrose. The latter is then separated from the remaining glucose and fructose solution by column chromatography and is crystallized by appropriate cooling (Stodola et al, 1956;Schwengers et al, 1990).…”

Section: Production and Specificationmentioning

confidence: 99%

Safety Evaluation Studies of Leucrose

Elias

Benecke

Schwengers

1996

Journal of the American College of Toxicology

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Leucrose, D-glucopyranosyl-a( 1 + 5)-~-fructopyranose, is produced by treatment of sucrose with the a( I + 6)-glucosyltransferase isolated from Leuconostoc mesenteroides, a nonpathogenic, nontoxigenic microorganism. Rats, dogs, and humans metabolize leucrose efficiently and rapidly in the jejunum by enzymatic hydrolysis into its constituent glucose and fructose. Only traces of leucrose appear in plasma and urine of rats and humans, whereas somewhat larger amounts are seen in plasma and urine of dogs. No toxic or other biological effects were detected in 13-week studies in rats and dogs. Leucrose is not teratogenic in rats and rabbits, and is not genotoxic. It is noncariogenic in humans and rats, and resists attack by the microorganisms present in the human oral cavity. Downloaded from SAFETY ASSESSMENT Microbiological ConsiderationsLeuconostoc mesenteroides is a species of the genus Leuconostoc that is nonpathogenic to plants, animals, and humans. The cell wall of dextran-forming strains contains dextran sucrase. The bacteria depend on the presence of a fermentable carbohydrate for growth. Dextran-forming strains occur on sugarcane and sugar beet as spoilage organisms. Leuconostoc mesenteroides forms a characteristic slime of dextran from sucrose. The genus is also nontoxigenic and is not known to form any bacteriocins or antibiotics. The use of this microorganism does not give rise to any microbiological hazards. Toxicological ConsiderationsLeucrose can be considered to be a modified sucrose, and therefore a food, that after digestion is present as glucose and fructose in the systemic circulation. The only structures in the body coming into direct contact with high concentrations of

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The Preparation, Properties and Structure of the Disaccharide Leucrose

Cited by 98 publications

References 0 publications

Cariological Assessment of Leucrose [D-Glucopyranosyl-α(1→5)-D-Fructopyranose] as a Sugar Substitute

Cariological Assessment of Leucrose [D-Glucopyranosyl-α(1→5)-D-Fructopyranose] as a Sugar Substitute

Sugar Alcohols

Safety Evaluation Studies of Leucrose

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