Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing saccharide radical
Patent
1990-07-27
1992-08-25
Robinson, Douglas W.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing saccharide radical
435822, C12P 1918
Patent
active
051418584
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a process for the enzymatic preparation of oligodextrans used in the production of sugar substitutes and to novel oligodextrans.
It is known to prepare dextrans of high molar mass, greater than one million (degree of polymerization greater than 6000 units of glucose) by the action of the lactic bacterium Leuconostoc mesenteroides on sucrose. It is also known that certain strains of this bacterium produce dextrans containing glucoside .alpha.(1.fwdarw.2) bonds, which constitute the branching points in these dextrans.
It was not known, however, prior to the present invention to carry out the enzymatic synthesis of oligodextrans (dextrans with a low degree of polymerization) containing at least one glucoside .alpha.(1.fwdarw.2) bond directly using sucrose and a sugar acceptor of glucose residues originating from sucrose.
The object of the present invention is to provide just such a process.
More precisely, the invention relates to a process for the preparation of a mixture of oligodextrans containing at least one .alpha.(1.fwdarw.2) glucoside bond and containing a major proportion of oligodextrans of the general formula (O-.alpha.-D-glucopyranosyl-(1.fwdarw.2)).sub.m (O-.alpha.-D-glucopyranosyl-(1.fwdarw.6)).sub.n A where A is the residue of a sugar acceptor of glucose chosen from amongst maltose, isomaltose, isomaltotriose, methyl .alpha.-glucoside and glucose, m is from 1 to 10 and n is from 1 to 30, the position of the .alpha.(1.fwdarw.2) glucoside bond or bonds being arbitrary, characterized in that sucrose and a sugar acceptor of glucose chosen from the group comprising maltose, isomaltose, isomaltotriose, methyl .alpha.-glucoside and glucose are brought into contact in the presence of glucosyltransferase enzyme extracted from at least one strain of the lactic bacterium Leuconostoc mesenteroides capable of producing, by fermentation, a dextran containing .alpha.(1.fwdarw.2) glucoside bonds, for approximately 2 to 48 hours in an aqueous medium.
The position of the glucoside .alpha.(1.fwdarw.2) bond or bonds in the formula indicated above is variable as a function, in particular, of the nature of group A and of the molar mass of the oligodextran, which itself is dependent on the reaction conditions. These bonds may, for example, be on the main chain, on the branches or may constitute the branching points in the oligodextran.
Non-restrictive examples of suitable strains of the lactic bacterium Leuconostoc mesenteroides are the following: NRRL B-1299, B-1399, B-1397, B-1298, B-1396, B-1424, B-1382, B-1149 and B-523.
Some of the oligodextrans (sometimes also called oligosaccharides) produced by the process of the invention are novel compounds. The preparation of O-.alpha.-D-glucopyranosyl-(1.fwdarw.2)-O-.alpha.-D-glucopyranosyl-.alpha. (1.fwdarw.6)-D-glucose trisaccharide by acetolysis of dextran NRRL B-1397 has, however, been described by K. Sakakibara et al. in Carbohydrate Research, 25 (1972), pages 443-451. Likewise, Y. Mitsuishi et al., in Carbohydrate Research, 127 (1984), pages 331-337, have described oligosaccharides branched by means of an .alpha.(1.fwdarw.2) glucoside bond.
The invention thus also relates to oligodextrans of the general formula (O-.alpha.-D-glucopyranosyl-(1.fwdarw.2)).sub.m (O-.alpha.-D-glucopyranosyl-(1.fwdarw.6)).sub.n A where A is the residue of a sugar acceptor of glucose chosen from amongst maltose and methyl .alpha.-glucoside, m is from 1 to 3 and n is from 1 to 10, the position of the .alpha.(1.fwdarw.2) glucoside bonds being arbitrary, as novel products.
The oligodextrans produced by the process of the invention which contain an .alpha.(1.fwdarw.2) glucoside bond which is located at their non-reducing end or which constitutes a branching point in the oligodextran, whether novel in themselves or not, are particularly resistant to enzymatic hydrolysis by glucohydrolase enzymes, such as endodextranase and glucoamylase, this resistance being due to the presence of this rare .alpha.(1.fwdarw.2) glucoside bond located at their non-reducing end or constitu
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Lopez Mungica Canales Agustin
Monsan Pierre F.
Paul Francois B.
Pelenc Vincent P.
Remaud Magali M.
BioEurope
Robinson Douglas W.
Saucier S.
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