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Preparation of D-Arabinose-1-C^14 and D-Ribose-1-C^14

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Preparation of D-Arabinose-1-C^14 and D-Ribose-1-C^14 Journal of Research of the National Bureau of Standards Vol. 51, No.6, December 1953 Research Paper 2458 14 Preparation of D-Arabinose-I-C'4and D-Ribose-l-C I Harriet L. Frush and Horace S. Isbell 1 By application of t he cyanohydrin synthesis to D-erythroso, D-arabinose-I-C14 a nd D­ t ribose-I-C" have been prepared in overall radiochemical yields of 30 and 8.5 percent, respectively. General acid catalysts in t he cyanohydrin reaction appear to favor format ion of t he ambonic epimer. The epimeri c acids res ul ting from the reaction of labeled cyanide and D-erythroso, and subsequent hydrolysis, were separated as crystalline potassium D­ arabonate-l-C14 and cadmium D-ribonate-l-C'4, respectively. The salts we re conver ted to the corresponding lactones, and t hese were red uced to t he sugars by usc of sodium amalgam in t he prese nce of sodi um a cid oxalate. 1. Introduction D-arabonate-l-C'4 was converted to D-arabono--y­ (" lactone-l-CI4, and this was reduced with sodium As part of it program to make position-labeled amalgam in the presence of sodium acid oxala te. 3 sugars available for research w'orkers in other labora­ A 56-percent yield of the crystalline D-arabinose-l-CI4 tories, methods have been developed at the National was separated without carrier ; by use of carrier, the Bureau of Standards for the preparation of D-glucose- radioch emical yield was increased to 60 percent. 1-CI4, D-mannose-1-CI", D-mannitol-l-C'4, n-fruc­ As potassium D-arabonate-l-CI4 was produced in 50- tose-l,6-C'\ lactose-l-C''', and D-arabinose-5-CI4 [1, percent yield, the over-all radiochemical yield of ~I 2, 3, 4, 5, 6).2 The present report gives methods D-arabinose-l-CI4 was 30 percent, based on Lhe for the preparation of D-arabinose-l-CI4 and n-ribose­ cyanide originally used. l_C I4. D-Arabinose-l-C I4 was required as an inter­ The cadmium D-ribonate-1-C'\ prepared from Lhe mediate in the preparation of D-glucose-2-C I4, and mother liquors of the potassium n-arabonate-l-CI4, both n ·arabinose-l -·C I4 and D-ribose-l-CI4 were n eeded was converted to D-ribono--y-lactone-l-CI4, which was for studies of the transformation of pentoses in brought to crys tallization by nucleation.4 The biological systems. R appoport and Hassid [7] lactone was reduced wi th sodium amalgam and gave obtained L-arabinose-l-C14 by application of the D-ribose-1-CI4 in 37-percent yield. Inasmuch as 23 Sowden-Fischer nitromethane synthesis [8] to L-ery­ pel'cen t of the activity of the cyanide had been tlu'ose. The L-arabinose-l-CI4 was separated in obtained as cadmium D-ribonate-l-C14, the over-all 3-percent yield by partition chromatography. radioch emical yield of D-ribose-1-CI4 was 8.5 percent. In ligh t of prior work at the Bureau, it seemed de­ Work still in progress will undoubtedly raise the sirable to attempt the synthesis of both D-arabinose­ yields of both cadmium D-ribonate and D-ribose-l-C14. l _C 14 and D-ribose-l-CI4 by th e cyanohydrin method, b eginning with D-erythrose. It was found that in 2. Experimental Procedures the reaction of cyanide wi th D-erythrose the presence of a general acid catalyst, such as bicarbonate or 2.1 Preparation of D-Erythrose ammonium ion, favors formation of the arabonic epimer. The epimeric products of reaction were For the preparation of sirupy D-erythrose, Sow­ separated by th e following steps: (1) Hydrolysis of den's m ethod of perioda te oxidation of a 4,6-substi­ the nitriles with aqueous sodium carbonate, (2) tuted glucose [9] was applied to 4,6-ethylidene-D­ passage of the solution over a cation exchange r esin glucose essen tially as described by R appoport and to give the free acids, (3) neutraliza tion of the acids Hassid [7], but wi th certain convenient modifi cations. r with po tassium hydroxide, and separation of labeled A mixture of 5.64 g of 4,6-ethylidene-D-glucose, mp D-arabonic acid as crystalline potassium D-arabonate, 180 0 to 1810 C [10] and 4.6 g of so dium bicarb onate (4) conversion of th e potassium salts in the mother was dis sol ved in an ice-cold solu tion con taining 11. 7 g liquor to cadmium salts by passage of the solution of sodium metaperiodate in 150 ml of water. The over a cation exchange resin, and neutralization of solution was kep t in an icc bath for a few minuLes, th e acid wi th cadmium hydroxide, and (5) separ ation and finally a t room temperature for 2.5 hr; it was then of the labeled D-ribonic acid in the form of crystalline freeze-dried. The fluffy residue was extracted with cadmium D-ribona te. a total of 150 ml of hot ethyl acetate in 3 portions. This procedure gave labeled potassium D-arabonate The extract was filtered through a b ed of decolorizing and cadmium D-ribonate in radiochemical yields of 3 In prev ious \'jPrk at t he Bureau , an cq ui molecu lar m ixture of 'Sodi um oxalate 50 and 23 percent, respectively. The potassium and oxalic acid was used as an internal neutral izi ng agent. Crystalline so1ium acid oxalate is a more co nvenient reagen t, and is rca:l il y prepared, although apparen tly not commcrciall y available. Usc of tlw aciel salt has res ulted in some­ 1 'I' he work descri bed in this papcr was sDonsored by the Atomic Energy what higher yie-Ids or the S l H~fl.r, pOSS ibly throu gh clo3er pH cont rol. CommiSS ion , givcn in ABC R eport NBS-2309. , We are indebterl to N . K . Richtmye r, of the N . tional Institntes of H ealth, , Figures in brackets indicate the literature references at the end or this paper. for seed cryslals of D-ribono-"),-Iaclono. 307 carbon and diatomaceous earth, and the solvent was TABLE 1. Effect of a general acid catalyst on the yield of the removed by distillation under reduced pressure. arabonic epimer obtained by the addition of cyanide to D-erythrose The residue, amorphous ~,4 - ethylidene-D-erythrose, was hydrolyzed by refluxmg for 1 hI' with 60 ml of Activity O.~-~ sulfuric acid; the hydrolyzate was cooled, and found in Experi­ carrier Arabonic deIOmzed by passage through a column of mixed Reaction mixture' potassinm epimer ment formed cation 5 and anion 6 exchange resins. The resulting D-arabon­ solution was concentrated under reduced pressure to ate b about 50 ml, and was then freeze-dried. The color­ Millimole. less sirup weighed 2.91 g and had a specific rotation o().0267 D-erythrose _______ ___________ __ } ;<C % { .0134 Na'CO'_______ _____________ ___ d 9.90 37.1 [a]~, ~'Jf - 17.3°. The cyanide-combining power of '.0267 NaCN_______ __________________ . '.0267 D-erythrose ____ ______________ __ } the SIrup was about 90 percent of the theoretical 2 { .134 (NH,l,CO, _____________________ d 14.80 55. 6 '.0267 NaCN ____ __ __________________ _ and consequently it was assumed that the residu~ ' 4.0 D-erythrose ____ ___________________ } contained 90 percent of D-erythrose. It was used { 10.0 NaHCO,_ _________ __ _____________ I 6,950 49. 6 without further purification for the cyanohydrin .3.1 NaCN ____ ____ _________________ __ _ synthesis described in the following sections. • Total v:olume was 1 ml in experiments 1 and 2, and 20 ml in experiment 3. b ActIVities determmed by means of a vibrating-reed electrometer after a modified Van Slyke-Folch wet oxidation procedure (see [11]). , Assuming 9O-percent purity of the erythrose sirup. d Calculated for entire 500 mg of carrier added. , Contained 26.7 ;<C of carbon 14. 2 .2. Effect of Genera l Acid Catalysts in the Cya n­ f Radioactivity recovered in several crops . ohydrin Synthesis on the Yield of the D-Arabonic • Contained 14 mc of carbon 14. Epimer 2.3. Preparation of Pota ssium D-Arabonate-l-C 14 from Several c~anohydr~n syntheses employing C14_ D-Erythrose by the Cya nohydrin Synthesis in the labeled cyamde and SIrupy D-erythrose were carried Presence of Sodium Bica rbon ate out on a semimicro scale under the conditions de­ scribed below. After hydrolysis of the cyanohydrins Ten milliliters of an aqueous solution containino- each mixture was treated with a large excess of non~ 3.1 millimoles of sodium cyanide (14.0 me of carbo~ radioactive potassium D-arabonate. From the ra­ 14) and 5 millimoles of sodium hydroxide was frozen dioactivity of the recrystallized potassium salt the on the sides of a small glass-stoppered tube. A proportion of D-arabonic acid was calculated. ' small lump of solid carbon dioxide was added, and The mixtures, two of which are listed in table 1 as tl?-en a solution containing 5 millimoles of sodium experiments 1 and 2, were frozen, and the tubes were bICarbonate and approximately 4 millimoles of D­ sealed and allowed to stand at room temperature for erythrose in 10 ml of water. The loosely stoppered 72 hr. They were then opened and heated on It flask was placed in an ice bath, shaken until the water bath at 80° C for 7 hI' in the presence of a contents had dissolved, and then kept in the bath stream of air.
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