CS240545B1 - Turanose and d-glucose preparation method - Google Patents

Abstract

The invention relates to a process for preparing turanose and D-glucose. The essence of the invention lies in the fact that % to 70 wt. aqueous solution of turanose and D- -glucose in 35 to 55 wt. ethanol chromatography selectively fractionate on the column ion exchange with functional sulfo groups in the calcium form from which it elutes 35 to 55 wt. ethanol, concentrated and crystallizes. The invention can find wide use in the study of biochemical processes bioengineering and medicine.

Description

The invention relates to a process for the preparation of turanose and D-glucose.

The invention is characterized in that 40 to 70 wt. % aqueous solution of turanose and D-glucose in 35 to 55 wt. ethanol is chromatographically selectively fractionated on a sulphonated ion exchange column in calcium form, from which 35 to 55 wt. ethanol, concentrated and crystallized. The invention can find wide application in the study of biochemical processes of bioengineering and medicine.

The invention relates to a process for the preparation of turanose and D-glucose.

Turanosis is a rare carbohydrate. Turanose is a non-reducing disaccharide of 3-β-α-D-glucopyrazonyl-D-fructose. In nature it is isolated. Most often it is prepared by partial hydrolysis of melezitose trisaccharide, from which the dehydrolysed D-glucose is fermented using the yeast Saccharomyces cerevisiae [E. Trap: Methods in Carbohydrates of Chemistry Vol. I, 353 (1962); Hudson C.S., E. Pascu: Science 69; 278 (1929); Hudson C, S. Pacsu, J. Am. Chem. Soc. 52, 2522 (1930); J.W. White: Arch. Biochem. Biophys. 80, 386 (1959). F. Rendoš, A. Ondrejkovič and Š. Bauer, prepared turanose by fractional crystallization of the partial hydrolysis of melezitose by ion exchange with sulfo-functional groups. [Cs. AO 158,005]. D-glucose is prepared by acid hydrolysis of sucrose or starch [W. B. Newkirk: Ind. Eng. Chem. 16, 1173 (1924); W. B. Newkirk, Ind. Eng. Chem. 28, 760 (1936); W. B. Newkirk, Ind. Eng. Chem. 31, 18 years (1939); Dean G.B. Gottfried: Advances Carbohydr. Chem. 5, 127 (1950);]. The aforementioned methods of preparing turanose are complicated and demanding in terms of chemicals and equipment. A further disadvantage is that turanose contained various colloidal substances which had to be laboriously removed.

The above-mentioned disadvantages are substantially eliminated by the process of preparing turanose and D-glucose, which consists in the fact that 40 to 70 wt. % aqueous solution of turanose and D-glycose in 35 to 55 wt. ethanol is chromatographically selectively fractionated on a sulphonated ion exchange column in calcium form, from which 35 to 55% w / w is eluted. ethanol, concentrated and crystallized.

The advantage of the proposed process for the preparation of toranose and D-glucose over the prior art is that it is simple, efficient and economical. It makes it possible to prepare both carbohydrates in one step as crystalline substances of high purity.

Example 1

To a solution of 25 g of melezitose in 250 ml of water is added 25 g of sulfonated functional ion exchanger (Wofatit KPS 200, 0.3 to 0.85 millimeters) and hydrolyzed at 80 ° C for 6 h with stirring. The hydrolyzate is collected by filtration. 2 g of this syrup are dissolved in 2 ml of a 35% strength by weight aqueous ethanol solution and applied to a column packed with a functionalized ion exchanger in calcium form (Dowex 50 Wx 8, 0.07 to 0.13). mmj and a column length of 100 cm and a column diameter

2.5 cm. The eluent used was 35 wt. aqueous ethanol solution. Using a fraction collector at a flow rate of 8 ml. h ^_1, the individual fractions collected descending paper chromatography (Whatman No. lj, the use of ethyl acetate: pyridine: water volume ratio of 8: 2: 1, and detect aniliniumhydrogenftalátom or 3,5-dinitrosalicylic acid spectrophotometrically at 575 nm. Fractions 14 and 30 contained 1 25 g of turanose and fraction 37-41 contained 0.60 g of D-glucose The fractions were individually concentrated on a rotary evaporator, purified by adding 0.5 g of activated carbon, filtered and crystallized with 5 ml of ethanol Turanose had an optical rotation [α] ²⁰ + M.p. 170 DEG-172 DEG C. and obtained in 95.4% yield D-glucose had an optical rotation [.alpha ^.] + ²⁰ DEG-53 DEG (c = 2 water); to 152 ° C and was obtained in 87.2% yield.

The procedure was as in Example 1 except that it was hydrolyzed at 90 ° C for 5 hours and 55% w / w was used as eluent. aqueous ethanol. Fractions 20-36 contained 1.22 g turanose and fractions 44-49 contained 0.58 g D-glucose. Turanose had an optical rotation [<a:] ²⁰ _D + 76 ° (c = 2 in water], melting point 171-172 DEG C. were obtained in a 93.1% yield. D-glucose had an optical rotation [i '] _D ²⁰ + 52 ° (c - 2 water), mp 150-152 ° C, and was obtained in 82.4% yield.

Example 3

The procedure is as in Example 1 except that it is used as the eluent

42.5% wt. aqueous ethanol. Fraction 17-28 contained 1.27 g turanose and fraction 40-48 contained 0.61 g D-glucose. Turanose had an optical rotation of [α] _D ²⁰ + 75 ° (c = 2 water), m.p. 170-172 ° C, and was obtained in 96.9 1% yield. D-glucose had an optical rotation (α _D ²⁰ + 53 ° (c = 2 water), mp 151-153 ° C and was obtained in 88.5% yield.

The invention can find wide application in the study of biochemical processes in bioengineering and medicine.

Claims (1)

SUBJECT A process for the preparation of turanose and D-glucose by hydrolyzing melezitose in aqueous solution by catalysing an ion exchange functionalized sulfo group, characterized in that 40 to 70 wt. aqueous solution of turanose and D-glucose at 35-55% w / w; ethanol chromatographically selectively graphically selectively fractionates on a sulphonated ion exchanger column in calcium form from which 35 to 55 wt. ethanol, concentrated and crystallized.