Jlarch 1966
255
NOTES
filtration and the filtrate was stored a t 0" under nitrogen. After evaporating part of the solvent under reduced pressure, the pure amine was isolated by preparative-scale gas chromatography on a 5-ft Carbowax column at 100"; nmr spectrum in CCla, 6 = 2.59 (s, CH3, 6 H), 6.03 (4, 2-H of ring, 1 H), 6.74 (9, 4-H of ring, 1 H), 7.15 (t, 5-H of ring, 1 H) ppm; J24 = 1.1 cps, J26 = 1.8 cps, Jas = 1.8 cps. Anal. Calcd for C6H8NO: C, 64.84; H, 8.16; N, 12.60; 0, 14.40. Found: C, 64.72, 64.64; H, 8.09, 8.03; N, 12.56, 12.57; 0, 14.61, 14.52. 3-Furyltrimethylammonium Iodide.-The amine was added to excess methyl iodide at 0" and the salt was recrystallized from anhydrous ethanol. No satisfactory melting point could be obtained; it started to turn brown at 160", with progressive decomposition above that temperature until a black mass was obtained a t 190". Anal. Calcd for CVHJNO: C, 33.22; H, 4.78. Found: C, 33.24, 33.09; H, 4.70, 4.78.
Poly--L-a,y-diaminobutyric Acid Hydrochloride MARGARET J. FRIDECKY ~ S D WILLIAMH. MCGREGOR
I'nion Carbide Research Institute, P. 0. Box 278, Tarrytown, .Vew York Receiaed October 18, 1965
The biocidal properties of polylysine and polyornithine' has prompted us to prepare a polymer of the next lower homolog. A crude poly-a, y-diaminobutyric acid had been prepared by Schmidt degradation of polyglutaniic acid? but the preparation of this polymer by polynierization of I\'"-carbobenzoxy-L-a, y-diaminobutyric S-carboxyanhydride has not been reported. The action of phosphorus pentachloride on i S " 1 Y dicarbobenzoxydiamiriobutyric acid yielded l-carbobenzoxy-3-carbobenzoxyaniinopyrrolid-2-oneand riot the expected S-~arboxyanhydride.~ More recently,j NY-tosyl-L-a,y-diaminobutyric acid was phosgenated mid then treated with hydrochloric acid resulting in a sequence of ring closure, opening, decarboxylation, and ring closure. The presumed intermediate, an Scarboxyanhydride ( S C A ) , was neither isolated or characterized but the results suggested the NCA could be prepared in this manner. The polymer was then synthesized by methods already described for polylysine6 except for minor details. The polymer mas an effective inhibitor of the growth of Alternaria species at levels of 0.501, (by weight) and caused lysis of Pamneciuni cauclatuin at levels equivalent to polylysine arid polyornithine (see Table I). The polymer was not attacked by trypsin or pepsin under the usual conditions. Experimental Section 11elting points are uncorrected. Elementary analyses were performed by Schwarzkopf llicroanalytical Laboratory. h i i n 0 acid analybis was performed by Analytica Corp.
(1) A I . S d a and E. Katchalski, A d a m . Protein Chem., 14, 391 (1959). ( 2 ) K. KO\-acs. G. Denes, A. Botai. and L. Polgar, Xaturwiss.. 42, 628
(1955). (3) E. Katchalski and M. Sela. Adoan. Protein Chem., 19, 402 (1958). (4) S.Wilkinson, J . Chem. Soc., 104 (1951). (5) K. Poduska and J. Rudinger, Collection Czech. Chem. Commun., 24, 3449 (1959). (6) G. D. Fasman. AI. Idelson, and E. R. Blout, J . A m . Chem. Soc., 8S, 709 (1961).
TABLE I ACTIVITY A G ~ I N S TParamecium caudatum Prepn
DPa
Poly-L-lysine 5-10 Poly-L-lysine 25 Poly->ornithine 25 Poly-L-a, 7-diaminobutyric acid 50 Streptomycin a Degree of polymerization. lysis in seconds.
Surrival oi paramecium' of prepn----Concn 10-5 .\I 10-4 .If 10-8
>3000 10-12 13-17
>3000 3-5 5-7
.\I
...
