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D-Glucuronic Acid. Crystalline Glucuronolactone

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D-Glucuronic Acid. Crystalline Glucuronolactone The Tohoha Journal of Experimental Medicine, Vol. 69, Nos. 2-3, 1959 Biochemical Studies on Carbohydrates CCXXVII. On Paper Chromatography of Rexuronic Acids By Hajime Masamune and Mei Satake (正 宗 一) (佐 武 明) From the Medico-chemical Institute, Tohoku University, Sendai (Received for publication, December 15, 1958) There were three papers published from this laboratory with respect to paper chromatography of glucuronic, galacturonic and mannuronic acids.1)-3) Since then, L-guluronic acid was isolated as L-guluronolactone from alginic acid,4) and L-iduronic acid in ƒÀ-heparine and skin-itinsulfate was identified by paper chromatography5) as well as by isolation as 2,3,4- tri-O-acetyl-L-idosan.6) Therefore the writers have investigated how to discriminate those five hexuronic acids occurring in nature in a paper chromatogram, with the resulting conclusions: 1) Kinds of filter paper made up of acid-treated fibers, for instance, Toyo Roshi filter paper No. 3 give concentrated spots contrary to those of filter paper without previous acid-treatment. 2) Free hexuronic acids are less sharply separated than their lactones by any of the solvent mixtures listed in Table I. 3) Solvent VI, VIII and ‡\ in Table I are most appropriate for the purpose, because they separate galacturonic acid from the remaining hexuronic acids on one hand and the lactones of the latter four hexuronic acids from one another on the other. Rr (rate of flow of a sugar against rhamnose) values of the hexuronic acids and their lactones are shown in the same table. 4) It is advisable to preliminarily free a hexuronic acid or acids from hexosamines, amino acids and ordinary sugars, which are present in the same hydrolysate, by the aid of a cation- and an anion-exchanger, if identification of them in mucoproteins is aimed at by paper chromatography. EXPERIMENTAL Hexuronic Acids as Materials D-Glucuronic acid. Crystalline glucuronolactone (Koso Chemical Co.) was taken up in water, NaOH was added to neutral from time to time to open the lactone ring, and thereafter sodium ions were eliminated by passing the solution through a column of Dowex 50 (H form), followed by dilution of the effluent to 1% with respect to the free hexuronic acid. D-Galacturonic acid. Crude barium galacturonate (amorphous) pre- 167 168 H. Masamune and M. Satake pared from beet pectin was freed from barium by the aid of an Amberlite IR-120 (H form) column, and after again adsorbing on a column of Am berlite IR-410 (acetate form), eluted by means of 0.1 N sulfuric acid. The eluate was collected in fractions. The Goldschmiedt positive fractions were united, the sulfuric acid was precipitated with excessive baryta, and the centrifuged supernatant was treated with the cation exchanger above and distilled in vacuo, whereupon a crystalline porridge (needles) was given. The product melted at 107-108•Ž and browned at about 153•Ž on further elevation of temperature. [ƒ¿]•‹D _??_ (initial, extraplated _??_ (at equilibrium). A l solution of it was prepared for the paper-chromatographic study. D-Mannuronic acid . A weighed amount of barium mannuronate (amorphous ; a gift from Prof. K. Aso in the Department of Agricultural Chemistry) was taken up in a volume of water, liberated from barium ions with Dowex 50 (H form) and diluted to 1 % with respect to the hexuronic acid as free acid. L-Iduronic acid. 10 mg. of 1,2-O-isopropylidene-L-iduronolactone (a gift from Prof. M. L. Wolfrom, Ohio) was suspended in 1 cc. of 20% acetic acid and refluxed for 160 minutes in a boiling water-bath. The hydrolysate was distilled in vacuo at a temperature below 30•Ž until it smelled no more of acetic acid. The still-residue was dissolved in 0.4 cc. of water, 0.01 N NaOH was added several times, each addition being stopped when the solution became neutral, and the sodium ions were removed by the aid of Dowex 50 (H form). The free hexuronic acid solution thus given was condensed as above to about 1 %. L-Guluronic acid. a) Preparation of sodium L-guluronate. 1.8 g. of 3,6-n-glucosaccharolactone (F.P. 132-133•Ž) prepared according to Kili ani7) was taken up in 20 cc. of water and transferred to a three-necked flask. The solution was chilled to 0-1 •Ž, and 60 g. of 2.5% sodium amal gam was added in small portions extending over 30 minutes under vigorous agitation, during which the temperature of the reaction mixture was maintained beween 3-6•Ž and the pH value of it between 3-4 by adding 20% sulfuric acid dropwise. After stirring for another 20 minutes under continuous chilling, the reaction mixture was filtered, and 10% barium acetate was added in small portions to the filtrate, until no more precipitate occurred. The centrifugate (BaSO4) was washed with changes of warm water, and the supernatant and washings (100 cc. in total) were passed through a 1.2 x 25 cm. column of Amberlite IR-120 (H form) to remove cations and washed. The effluent and washing were concentrated to a syrup, diluted with 30 cc. of water and neutralized with the saturated On Paper Chromatography of Hexuronic Acids 169 baryta. The centrifuged supernatant and the washing of the centrifu gate were combined (63 cc., pH 6.8), added to a 2.6 X 19 cm. column of Dowex 1 (acetate form), and after washing with 100 cc. of water, eluted with 0.3 N acetic acid at a flow rate of 2 cc. per minute. The eluate was collected in 50 cc. fractions. Frs. Nos. 10-19 which were Goldschmiedt positive were distilled together in vacuo at a temperature below 35•Ž to a thick syrup. It was then dissolved in 5 cc. of water, neutralized carefully with 1.0 and 0.1 N solutions of NaOH to a constant pH value of 7.2 and distilled as above to about 1 cc. The condensate containing some crystals in needles was stood overnight in a refrigerator, and the crystalline porridge was filtered off under chilling and washed with dilute methanol and abs. methanol in succession. Yield 570 mg. F.P. 124-125•Ž (gas evolution). Recrystallized twice from water, it melted constant at 125.5-126•Ž (gas evolution). _??_ No mutarota tion took place. Found: C, 27.22; H, 5.18; ash (Na2SO4) (Pregl), 27.33; crystal water, 9.92 (loss at 105•Ž in vacuo over P2O5 for 5 hours). C5H9O7Na•E2 1/2H2O requires C, 27.59; H, 5.40; ash 27.20; crystal water, 17.25. C and H were kindly analyzed by Mr. H. Obara Assistant in the Chemical Department according to Pregl, for which the writers are in debted. b) Free guluronic acid. A solution of sodium guluronate was freed from sodium by the aid of Dowex 50 (H form) and diluted to 1 % with respect to the free acid. c) L-Guluronolactone. L-Guluronic acid does not readily change into lactone when stored as a solution (examined by paper chromatography). Therefore a part of the 101 solution of L-guluronic acid was evaporated to dryness on a boiling water-bath and further placed in a vacuum-desiccator containing anhydrous calcium chloride for 2 days. The substance thus given was dissolved in water and diluted to I%. Method of Paper Chromatography (7-10.5) x 56 cm. slivers of Toyo Roshi filter paper No. 3 were each spotted at a distance of 10 cm. from the upper edge with a volume, con taining 200-300 y in total of a hexuronic acid and its lactone as hexuronic acid, of one of the above solutions, which had been stored in a refrigerator for several days after preparation. Each of the slivers was also spotted in a similar manner with a 200 y amount of rhamnose Takeda side by side with the spot above, and each spot covered an area about 0.8 cm. in dia meter. Next the rectangular trough in the same apparatus as the one illustrat ed by Masamune and Yosizawa3) was filled with one of the solvent mixtures 170 H. Masamune and M. Satake in Table I, which had been stored for more than 2 weeks at room tem perature, and after covering with the bell (The spotted paper-slivers were not hung on the trough), placed in an air thermostat at 24-27•Ž for 12 hours until the atmosphere of the chamber was saturated regarding the solvent. Then the apparatus was opened and quickly set up, dipping the upper edge of the slivers in the solvent and shutting with the bell. The chromatograms developed in a descending way. Temperature of test the same as above. Duration of test 5-15 hours. Indicator aniline hydro- gen phthalate reagent of Partridge8) or p-anisidine phosphate reagent of Mukherjee and Srivastava.9) Result In Table I are embodied average Rr values of hexuronic acids and their lactones by various solvents, which had been calculated after 3-8 runs of chromatography with each solvent regarding each hexuronic acid. Fig. 1 is plotted from those figures. DISCUSSION AND REMARKS 1) Fischer and Dorfel10) disapproved our previous reportS2),3>, saying that spots of hexuronic acids tail and diffuse by the solvents in those re- ports. Such an inconvenience occurs as a matter of fact, when such papers as Toyo Roshi filter paper Nos. 2, 50 and 51 which are untreated with acid are used, but does not when the acid-treated Toyo Roshi filter paper No. 3 and the alike are used, as is generally the case in paper chromato graphy of organic acids.") 2) Masamune and Yosizawa3) obtained Rr values of D-mannurono lactone and D-glucuronolactone in reversed relationship with those of the same lactones in this account.
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