Isomaltulose

Isomaltose [499-40-1] Isomaltulose Isomanmde Isomar process Isomenthone [491-07-6]... 

The synthesis of some commercially important bulk sweeteners such as isomaltulose (Palatinose), isomaltitol (Palatinit), and Actilight (formerly Neosugar) has been achieved by enzymatic transformations of sucrose. 

Isomalt, a mixture of a-D-glucopyranosyl-l,l-D-mannitol dibydrate and a-D-glucopyranosyl-l,6-D-sorbitol, is obtained by hydrogenating isomaltulose which is en2ymatically derived from sucrose (102). 

C12H22O1 j H2O 6-O-a-D-Glucopyranosyl-a-D-fructofuranose, monohydrate (isomaltulose, monohydrate palatinose, monohydrate) IMATUL 31 352... 

Sucrose isomerase (Sucrose mutase) Isomaltulose 100,000 Sudzucker, Cerestar (Germany) Mitsui Seito Co (Japan)... 

B. A. Lina, D. Jonker, and G. Kozianowski, Isomaltulose (palatinose) A review of biological and toxicological studies, Food Chem. Toxicol., 40 (2002) 1375-1381. 

D. Zhang, X. Li, and L. H. Zhang, Isomaltulose synthase from Klebsiella sp. strain LX3 Gene cloning and characterization and engineering of thermostability, Appl. Environ. Microbiol., 68 (2002) 2676-2682. 

Therefore, taking into account the potentialities of such lactones as carbohydrate delivery synthons (vide infra), several routes leading to carboxymethyl glycosides (and thus subsequently to the lactones) were investigated, in order to get as many structural variations as possible for widening the scope of their use in synthesis. In addition to the isomaltulose oxidation method (route a), the oxidation of allyl glycosides (route b), and the anomeric alkylation with tert-butylbromoacetate (route c) were studied (Scheme 11). These three methods are detailed in the following sections. 

Oxidation of isomaltulose and related sugars synthesis of CMGlu and CMGL... 

Disaccharides such as isomaltulose (6-a-D-glucopyranosyl-D-fructo-furanose), obtained in one step from sucrose by bioconversion (Scheme 12),44 Isomalt , the hydrogenated derivative of isomaltulose and trehalulose (1-a-D-glucopyranosyl-D-fructopyranose) have been shown to be interesting substrates for chemistry.45... 

Scheme 2.17 Generation of isomaltulose from sucrose, and the foUow-up products with industrial potential.

Another, industrially relevant foUow-up reaction of isomaltulose comprises its ready conversion into 5-(a-D-glucosyloxymethyl)-furfural ( a-GMF ) by acidic dehydration of its fructose portion under conditions (acidic resin in DMSO, 120°C ) that retain the intersaccharidic linkage (Scheme 2.17). As this process can also be performed in a continuous-flow reactor,a most versatile building block is available from sucrose in two steps, of which the first is already industrially realized, and the second simple enough to be performed on a large scale. 

Scheme 2.18 Isomaltulose-derived products with surfactant and liquid crystalhne...

Lichtenthaler, F. W. Klimesch, R. Muller, V. Kunz, M. Disaccharide-building blocks from isomaltulose glucosyl-a(l—>5)-D-arabinonic acid and ensuing products, Liebigs Ann., 1993, 975-980. 

In the context of the strong commercial interest in alternative sweeteners, in particular isomaltulose (which is produced industrially by the conversion of sucrose with the sucrose isomerase SmuA from Protaminobacter rubrum, a GH 13 enzyme), the complex with 1-deoxynojirimycin (2, 10 pM) was investigated (PDB 3GBE)278... 

Acetylation of the latter compound led to bicyclic lactone 129. Another lactone 130 was also observed as side product when the oxidative degradation of the fructose moiety of isomaltulose was incomplete [186]. 

Isomaltulose Isopanose glucopyranosyl-( 1— 6)-D-glucopyranose 0-a-D-Glucopyranosyl-( 1 — 6)-D-fructofuranose 0-a-D-Glucopyranosyl-(l- 4)-0-a-D-glucopyranosyl-(1 - 6)-D-glucopyranose... 

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