COMMUNICATIONS TO THE EDITOR
Feb., 1047
473
.l complete study of the applicability of the synthetic method outlined above is in progress.
there was obtained by acetone elution and crystallization from ethanol, a substance crystallizing in tufts of fine needles; m. p. 134-13Ao, mixed THEBAKERLABORATORY O F CHEMISTRY CORNELL UNIVERSITY A . T. BLOMQUIST melting point with 6-a-D-glucopyranosido-/?-DSEW YVRK ITHACA, R. D. SPEXER glucose octaacetate 120-125', [ N ] * ~ D 86' (c RECEIVED JANUARY 20, 1947 1 .6, chloroform). This material is the hendecaacetate of a trisaccharide and its structure is under further investigation. THE CRYSTALLINE OCTAACETATE OF Anal. Calcd. for C ~ ~ H ~ I O I ~ ( C H : C, ~ 49.69; CO)~~ 6-CY-D-GLUCOPYRANOSIDO-P-D-GLUCOSE H, 3.63; mol. wt., 966.8. Found: C, 49.46; H, - -Sir: 331 ; mol. wt. (Rast), 971. The polysaccharide dextran ( [ a I 2 O ~ lS0O; OF CHEMISTRY DEPARTMENT L. LV. GEORGES c I , water) produced by Leuconostoc dextranicum THE OHIOSTATEVTNIVERSITY I. L. MILLER was hydrolyzed a t room temperature in %yo solu- COLUMBVS, OHIO M. L. U'OLFROM tion in 30yo hydrochloric acid to approximately RECEIVED JAXUARY 17, 1917 two-thirds completion ( [ a ] " " D of solution 10.7'). -After removal of inorganic ions by successive treatment with lead carbonate, hydrogen sulfide, THE ANTIBACTERIAL ACTIVITY OF +AMINOBENZENEPHOSPHONOUS ACID sodium bicarbonate and -1mberlite resins (IR-100 anti TR-J), the D-glucose was removed by yeast Sir : fermentation and the sirup obtained on solvent It has been shown by Kuhn, AIoller and Wendt' removal was acetylated with hot acetic anhydride that phosphanilic acid (P-H&JC6HaPO(OH)z) has and sociium acetate. The resultant mixture of a slight antibacterial action, similar in nature to sugar acetates was chromatographed' on Magne- that of the sulfonamides in being antagonized by solLCelite employing benzene-ethanol develop- p-aminobenzoic acid. Proceeding on the assumpment under such conditions that any monosac- tion that the strength of the sulfonamide-enzyme charide prescnt would be removed from the col- complex is increased with decreasing acidity,? we umn. The material from the lowest zone was have prepared p-aminobenzenephosphonous acid, rechromatographed in similar fashion and the p-H?NCaHIP(OH)2,by the procedure lowest zone material again obtained was crystalAlC1, H>O lized (elongated prisms) from ethanol; m. p , ChH,Br + PCl? p-BrCeHJ'C12 14:3-144", [ a ] % ) 97' (c 2 . 7 , chloroform). p-BrCeHAP(OH), (1) Anal. Calcd. for C12H14011(CH3CO!S: C, cui0 4!i,.X; H, 5.63; CHJCO, 11.79 cc. of 0.1 S so- p-BrCaHZ(OH I 2 SHlOH ~-H&CSH~P(OH)~ dium hydroxide per 100 nig.; mol. wt., (iiS.($. (2) Found: C, 49.74; H, 5.(ji; CHJCO, 11 The first step, the preparation of p-bromobenzenemol. wt. (Kast), 6SO. Since methylation ~ t u d i e shave ? ~ ~ demonstrated phosphonous acid, has been carried out previ~ second step, the synthesis of the that the polysaccharide employed in this wdrk is o ~ s l y . The built up of a-D-glucopyranose units linked in the amino compound, is similar to that used by 1,&position, it follows that the disaccharide iso- Bauer4 to prepare phosphanilic acid. lated must be (i-a-D-glucopyranosido-8-D-glucose The product obtained has these properties. octaacetate. Its determined rotation is in agree- m.p. 169'; eqilivalent weight, calculated 157.1, ment with the value predictable by application of found 158.0; analysis, calculated P 19.TIC&,found thc, isomtation rules of Hudson. The same acet- P 19.6674; solubility in water a t 0' about .jq; ylation and chromatographic procedure was ap- ph-,3.6s. The activity of p-arrinoben7enephosphonous plied to the sirup soluble in SO' ethanol that was ?.btained essentially according to the procedure of acid was tested against E coli arid found to be Ortenblad and liyrbackf from the enzymic hy- slightly less than that of sulfanilamide. This tlrolyzate o f amylopectin (waxy maize) after re- antibacterial action was antagonized by p-aniinonova1 of most of the maltose and D-glUCoSe by benzoic acid a t concentrations approvimately yeast fermentation. I n this case the lowest zone equal to those necessary to counteract sulfanllun the chromatogam was composed of @-maltose amide. Further tests on this substance and reoctaacctate (m.p. 1.Y-160°, mixed rntlting point lated compounds are in progress. OF CHEMISTRY l Z I - l f i O O un!.hangcd; [a]"D W 0 ,c 1.1, chloro- DEPARTMEYT I M KLOTZ zone immediately above this NORIHIYESTERN UKIVERSITY
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TT. Binkley and M. L. Wolfrom, THIS 61, > L i ' 1 ( 2 , E. c'. F i r h e a d , 11. J Hunter and H. Hibbert, Can. J . I&q ~ c ~ r
