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The Fact That D-Ribose Is One of the Important Constituents of Ribonucleic

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The Fact That D-Ribose Is One of the Important Constituents of Ribonucleic The Journal of Biochemistry , Vol. 36. BIOCHEMICAL STUDIES ON d-RIBOSE, WITH SPECIAL REFERENCE TO THE MECHANISM OF ABSORPTION OF SUGARS FROM INTESTINAL TRACT. BY YOSINORI NAITO. (From the Department of Biochemistry, Niigata Medical School. Director: Prof. N. Ariyama.) (Received for publication, July 12, 1942.) The fact that d-ribose is one of the important constituents of ribonucleic acid as well as of various co-enzymes, gives this pentose a special, biochemical significance. Our knowledge on the meta bolism of this sugar is, however, still very limited, when compared with the brilliant results attained in the chemical study of the sugar. Hamburger (1922) observed that a part of ribose perf used through the frog kidney was retained by the tissue. Raymond and Blanco (1928), and Dickens (1938) found that ribose was not fermented by living yeast. Ribose-5-phosphoric acid was found by Dickens (l. c.) to be fermentable by the Lebedew extract, one molecule of the substrate producing one molecule of ethyl alcohol, carbon dioxide and phosphoric acid respectively along with a substance or substances of unknown nature. The increasing interest on the metabolism of ribose has prompted a further in vestigation, the results of which will be published in this paper. EXPEEIMENTAL. I. Synthesis of d-ribose. d-Ribose employed in the present experiment was synthesized from gluconic acid. In the first stage of the synthesis, calcium gluconate was converted into d-arabinose by the Hockett and Hudson method (1934). The yield was 100gm. of d-arabinose from 350gm. of calcium gluconate dihydrate. d-Arabinose melted 131 132 Y. Naito: at 155-156•Ž. [ƒ¿]20D-103.3•‹. d-Arabinose was then oxidized to arabonate by bromine in the conventional fashion. The yield was 100gm. of calcium d-arabonate from 100gm. of d-arabinose. In the meanwhile, it was found that the addition of 10% more calcium carbonate than the calculated value increased the yield of arabonate. From the next stage on, the operation followed the Steiger method (1936). Arabonate was epimelized to ribonate and the acid was then converted into cadmium salt. It was found advisable to put the salt through a rigorous process of purification so as to perform the following operations more easily and to increase the yield of the products. The yield was 24gm. of pure cadmium ribonate from 100gm. of calcium arabonate. Crystalline lactone of ribonic acid was derived from the cadmium salt. The yield was 12gm. of lactone from 24gm. of cadmium salt. The lactone was finally reduced to d-ribose with sodium amalgam. When the purest sam ple of lactone was used, ribose crystallized out directly upon inoculation; otherwise the sugar was obtained in a syrupy state. The yield was 12gm. of the syrupy ribose or 8gm. of crystalline ribose from 12gm. of lactone. The crude ribose was purified through p-bromophenylhydrazone, and repeatedly recrystallized from alcohol, until the fusing point reached the constant value. The yield was 4-5gm. of pure d-ribose from 12gm. of the syrupy crude ribose or from 350gm. of calcium gluconate. II. Some physical properties of d-ribose. FP=86-88•Ž. (uncorr.)-Levene and Jacobs (1909): 86 87•Ž. (corr.); van Ekenstein and Blanksma (1913): 95•Ž.; Phelps et al. (1934): 87•Ž. [ƒ¿]18D-21.4•‹(H2O, 2.57%, 2dm) Levene and Jacobs (l. e.): [ƒ¿]D-19.5•‹ (H2O, 4%); van Eken stein and Blanksama (l. c.); [ƒ¿]D-21.5•‹; Kuhn et al (1935) [ƒ¿]22D-22.5•‹ (H2O, 0.9%). III. Some chemical properties of d-ribose. The reducing powerr of ribose against the Somogyi reagent (1926) was 90.5% of that of glucose. This value was reached Biochemical Studies on d-Ribose. 133 after 35 minutes' heating; the value after 15 minutes was 85 .3%. Levene and Jorpes (1929) stated that the reducing power of ribose against the Hagedorn-Jensen reagent was equivalent to 87.3% of that of glucose. Ribose was more sensitive to alkali than other pentoses. It is revealed in Table I that at 0 .5n sodium hydroxide-alkalinity and at 20•Ž., the reducing power of the 0.5% ribose solution decreased more rapidly than those of d-xylose, and of d and l-arabinose. The velocity of the conversion of pentoses into furfural was followed, according to the Hoffman method TABLE I. Decrease of Reducing Powerr of Pentoses in Alkaline Medium. 5cc. of 1% pentose solution+5cc. of n NaOH. 20•Ž. Determination of reducing power: Somogyi's method. TABLE II. Production of Furfural front Pentoses (Hoffman's method). 134 Y. Naita: (1927), by distilling sugars with 20% hydrochloric acid and by determining furfural colorimetrically with aniline acetate. As shown in Table II, the conversion was most rapid in the case of ribose. The almost quantitative production of furfural was achieved after one and a half hours' distillation, while the con version by this time was about 90% in xylose, and about 50% in d- and l-arabinose. Ribose in purine nucleosides and purine nucleotides of the yeast origin was found by Hoffman (I. c.) and Ishikawa (1935) to be also quantitatively determinable by the furfural method, though the rate of the production of furfural was more or less retarded by the presence of purines and phosphoric acid which combined with the sugar. Younburg (1927), and Andrews and Milroy (1933) were unable to carry out the 100% conversion of free and combined ribose into furfural. This may be due to the incomplete formation of furfural from ribose under different condition from that of the Hoffman method. IV. Biological properties of d-ribose. The minimum quantity of ribose, which caused pentosuria after the intravenous injection to the marginal veins of rabbits starved for 24hours, was 250mg. per kilogram of body weight. The oral administration of 2gm. of ribose per kilogram of body weight by the stomach tube did not yet produce definite pentosuria. The tolerance for other pentoses was much lower than that of ribose; less than 50mg. per kilogram of body weight in the case of the in travenous injection of d-xylose and d-arabinose, and less than 0.5 gm. in the case of the oral administration. The excretion of sugars was examined by determining the increase of the non-ferment able reducing power of the total urine which was collected by combining the portion excreted during the experimental period and the portion catheterized from the bladder at the end of the period. The far higher tolerance of ribose suggests the much greater utilization of this sugar than other pentoses in the animal body. The influence of the intravenous injection and the oral ad ministration of ribose on the blood sugar of rabbits which had been starved for 24hours was examined. The protocol of an experiment Biochemical Studies on d-Ribose. 135 TABLE III. Intravenous Injection of d-Riose to Rabbit. Ribose: 250mg. per kg. Rabbit: 2450gm., ?? . Extra-excretion of non-fermentable reducing substance in urine during 7hours: 48mg. in terms of glucose. TABLE IV. Oral Administration of d-Ribose to Rabbit. Ribose: 2,0gm. per kg. Rabbit: 2300gm., ?? . Extra-excretion of non-ferm. red. subst. in urine during 8 hrs.: 5mg. in terms of glucose. 136 Y. Naito: fairly typical for each case is listed in Table III and IV respec tively. The values of the non-fermentable sugar which had been raised by the introduction of ribose, fell to the normal level more rapidly than those of the fermentable sugar which had also in creased. The blood sugar was determined by the Hagedorn Jensen method. Table V and VI indicate that a marked appear ance of d-arabinose and a moderate increase of the fermentable sugar in the blood were induced by the introduction of a small amount of the sugar, and that the curves of arabinose receded to the original value more quickly than those of the fermentable sugar. The increase of the fermentable sugar caused by injection and administration of d-xylose and l-arabinose has been repeatedly observed in rabbits and rats by many investigators-Corley (1926, 1928), Blanco (1928), Fishberg (1930), Miller and Lewis (1932 ii), Larson and Sawyer (1936). Sawyer (1940) stated that the administration of l-xylose to rats did not produce hyper glucemia. The absorption of ribose from the intestinal tracts of rats was studied. The procedure was somewhat modified from that describ TABLE V. Intravenous Injection of d-Arabinose to Rabbit. Arabinose: 50mg. per kg. Rabbit: 2300gm., ?? . Extra-excretion of non-ferm. red. subst. in urine during 4 hrs.: 37mg. in terms of glucose. Biochemical Studies on d-Ribose. 137 TABLE VI. Oral Administration of d-Arabinose to Rabbit. Arabinose: 1gm. per kg. Rabbit: 2750gm., ?? . ed by Cori (1925). Rats, weighing from 100 to 150gm. after having starved for 48hours, received 2cc. of the 25% sugar solu tions with the aid of a stomach tube (urethral catheter No. 5). The loss of the sugar adhering to the catheter was 5% of the total sugar on an average taken from 10 control experiments. The amount of the sugar absorbed was calculated from the difference between the quantity of the sugar given and that remaining in the stomach and the entire small intestine. The large intestine was discarded, since the quantity of the sugar, found there, was negligible, and there remained a good quantity of intestinal contents which gave a reducing power corresponding to 5 to 10mg. in terms of glucose. The reducing substance present in the stomach and the small intestine of fasting rats was 0.80mg. and 3.78mg. respectively in terms of glucose on an average taken from five experiments. The absorption of the sugar was determined 1 and 2hours after the feeding, and the absorption coefficients (C) were calculated by the following formula of Cori: C=A•~100/W•~ T 138 Y.
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