CS260699B1 - A method for preparing 1,6-anhydro-1-D-glucopyranose labeled with radioisotope 14θ - Google Patents

Abstract

The labeled starch, originating from photoautotrophic organisms, preferably from the green alga Chlorella vulgaris, is pyrolyzed, preferably at a temperature of 350 to 450 °C, under a pressure of 0.1 to 1 kPa, preferably for the time necessary to carbonize the starch, after which the product is isolated from the resulting liquid portion.

Description

The present invention provides a process for the preparation of 1,6-anhydro- [beta] D-glucopyranose 14 labeled with radioisotope C.

1,6-Anhydro- (3-D-glucepyranose) is an extremely synthetically useful substance which is useful for the preparation of a number of otherwise rarely available rare carbohydrates and their derivatives / Černý M., Staněk J., Jr .: Advan. and Biochom., 34, 23, 1977 // ·

literature described ·

It could be used to prepare, for example, 2-substituted-2-deoxy-derivatives of D-glucose and 3-substituted-3-deoxy-derivatives of D-glucose, D-nannose and D-galactesis labeled with ¹ ^ C radioisotope. 2-deoxy- and 3-deexyaldes.

Unlabeled 1,6-anhydre-O-D-glucepyranes (so-called levoglucosan) can be prepared by pyrolysis of starch or cellulose from reduced pressure (Pictet A., Sarasin J. Helv. Chim. Acta 1, 87 (1918), Gardiner D.i J. Chem. Sec. 1966. 1473) and has been described among the products of pyrolysis of D-glucose and various oligo- and polysaccharides (Dialer R.J.,

Davio, H. A., Hilbort, G. E., J. Amor. Chem. Sec. 68, 1377 (1946), Dimler R. J. Advan. Carbehyd Chem. 2 »37 (1952), Bryce D.J., Groenwood C.T .: Starko 12, 275 (1965), Thompson A., Wolfram M.L .:

J. Amor. Chem. Sec. 80, 6618 (1958)] and between the products after heating the methyl-M-D-glucopyranoside in dimethylsulfoxide (Fischer M.H .: Carbehyd. Ros. 8, 354 (1968).

- 2,280,699

Another method for the preparation of 1,6-anhydro-β-D-glucopyranoay utilizes alkaline hydrolysis of phenyl totra-O-acetyl-β-D-glucepyraneside / Coleman GH: Methoďa Carbahyd. Khan. 2 _t 391/1963 //

Most ecanically, the scratch pyralysis, which aa achieves in practice a calenene yield of 25% / Ward R.B .: Metheda Carbahyd. Khan. 2, 394 (1963) // At higher scrape weights (above 200 g) and yields of 1,6-anhydr β-β-D-glucepyraneay rapidly decrease.

Moisture of the scratch also adversely affects the yield.

Preparation of 1,6-anhydre-Z3-D-glucepyraneay, radiolabelled

C, would require what kind of starting-labeled scraper.

It is a preferred source of feteautetref erganis, for example, the algae Chlarella vulgaria (AO 121 808).

In the case of pyralysis, it would be easier to start from the order of milligrams of labeled scratch, thus making it more efficient to dry and, in particular, more efficient pyralysis.

Based on these facts, the proposed process for the preparation of 1,6-anhydre-β-D-glucepyraneae labeled with radieisetep, the essence of which is that a labeled hake originated from feteautetrephal erganisins, and benefits from green algae of Chlarella vulgaria, pyrellizes and preferably at 350 to 450 ° C at a pressure of 0.1 to 1.0 KPa, preferably for the time necessary for starch retention, and then isolating the product from the resulting liquid.

The advantage of this method for the preparation of radiolabelled labeled 1,6-anhydr E- (3-D-glucose) is that

- it uses a relatively deatupine and economically advantageous starting material,

- allows radiochemical yields of about 30%.

- 3 Example

280699

Lyophilized starch (178 MBq $ 3.2 mg), isolated from green algae of Chlorella vulgaris Beijarine cultivated in an atmosphere, was pyrolyzed in a disposable glass apparatus, consisting of a tube per acting boiled sealed and expanded in a flask / in this section a sample was placed (further passing U-shaped) in this part, which was cooled in January, the liquid fraction of pyralysis was collected (and the second boar connected to a vacuum source (alley vacuum pump).

The scratch sample was heated with a flame gas burner so that the temperature in the hearth of the heating reached 380-420 ° C while maintaining the apparatus pressure at 0.5 to 0.6 kPa.

Pyrolysis was carried out until the starch sample was carbonized.

The U-tube from the entrapped liquid fraction that passed into the air raid was cut off, its leached content leached with ethanol and the amount of radioactivity corresponding to 78.7 MBq / 44% / was found in the solution.

The liquid fraction was further analyzed by paper chromatography in 1-butanol-ethanol-water (52: 33: 15), 1-butanol-pyridine-water (6: 4: 3) and 1-butanol-acetic acid-water / 4: 1: 5 / against standard unlabeled 1,6-anhydro-3-D-glucopyranose found on average 69% content of 1,6-anhydro-PD- U ^ - ^^ _t cJglukopyranooy i.e. 30.5% on the starting starch.

Proportative paper chromatography in a 1-butanel-pyridine-water system (6: 4: 3) was isolated with 44.6 MBq (25%) of 1,6-anhydro-β-D- [beta] -copyrides in the morning sy.

SubjectSize

Claims (1)

A process for the preparation of 1,6-anhydre- (3-D-gl) in the morning with a radiolabelled ¹⁴ ° C, characterized in that the labeled starch is derived from photoautotrophic organisms, preferably green algae Chlorella vulgaris, pyrolysis is preferably at a temperature 350 to 450 ° C, at a pressure of 0.1 to 1 kPa, and preferably for the time necessary to carbonize the starch, whereupon the product is isolated from the resulting liquid fraction.