COMMUNICATIONS TO THE EDITOR
1868 12.20.
Found? C, 63.93, 64.07; H, 4.22, 4.30; S, 12.20,
1 0 i'i I Y . l l .
Oxidation of the sulfide with 30% hydrogen peroxide (Superoxol) in :teetic acid-acetic anhydride gave p&lorophenyl phenacyl sulfone, m. p. 133-134 (previously pre-_
(3) Microan'tlyses by Dr. Carl Tiedcke, Pu'ew York, N Y
Vol. 68
pared by a different method, m. p. 132-133').' (4) Troger a n d Beck, J . prakt Chem., [2] 87, 206 (1913)
ENGINEERING ISAIAHVON PHILADELPHIA 4, PENNSYLVAXIA MARVIN CARMACK RECEIVED APRIL25, 1946 DEPARTMENT OF
UNIVERslTy
CHEMISTRY A S D CHEMICAL OF PENssYLVANIA
___-
COMMUNICATIONS T O T H E EDITOR GROWTH INHIBITION OF LACTIC ACID BACTERIA .. __- -BY N- ( 3 ,y-DIHYDROXY-B&DIMETHYLVALERYL)-pALANINE AND ITS REVERSAL BY PANTOTHENIC ACID' ~~
TABLE I
~
Sir: It has been observed that pantothenic acid molecules with modified lion-nitrogenous moieties exhibited diminished or inappreciable growth Salicylol-P-alanine and mandelyl-0alanine have been reported to be effective displacers of pantothenic acid.4 A few analogs possessed inhibit.ory properties but their effects were not reversed by pantothenic acid.3 In the present studies, the growth of lactic acid bacteria was inhibited markedly by N-( a ,y-dihydroxy-P,Pdimethylvalery1)-&alanine and the inhibition was reversed, competitively, by pantothenic acid over a wide range (of concentrations. a,a-Dimethyl-fi-hydroxybutyraldehyde (b. p. 74-77' (15 mm.)), prepared as described by Lilienfeld arid ' I ' a ~ s s , ~was converted to ahydroxy-0,fi-diinetliyl-y-valerolactone (b. p. 93-94.5' (1 nini.)) by the method of Stiller, et d 6 The lactone crystallized from diethyl etherpetroleum ether as white hygroscopic needles. Anal. Calcd.. for C7HI2O3: C, 58.31; H, 5.39. Found: C,, 57.(i9; H, 5.47. The sodium salt of dl - N - ( a ,y - tlihydroxy - /3,@ - dimethylvalery1)fi-alanine was prepared by fusing a iiiixture of the lactone and the sodiuiii salt of @-alaninea t 110120O. Acid production (nil. of 0.0385 iV base to titrate final 3-ml. volumes) is shown in the Table I. Mixtures of the lactone and 0-alanine had little effect in concentrations as high as 10,000 y per tube. It is of interest that stimulations occurred a t low levels (of the analog in the presence of pantothenic acid. Phenyl pantothenone has been reported to be stirnulatory a t sub-inhibitory level^.^ (1) Aicleil by yrauts f r c m the Natiounl Iristitutr oi He;illh ( i f t h e ( J , S. Public H e i l t h Service a n d t h e l J uf Ci1liforoi.i ( l a ) Williarna, .Idn. 211 E m y i i i . , 3, 263 (1'943). ( 2 ) Nease, Dissertation, U. of Texas (1943); quoted by Snell and Shive, J . Biol. Cht,m., 158, 551 (1945). (3) McIlwain, 13iochem. , A ) h l a r t i n , I.t=n.is aud 1 Papers, 1179th Meeting, :1m. Chem. S u i . , L'IU ( l Y 4 t i ) . ( 5 ) Lilienfeld a n d Tauss, Monalsh., 19, 77 (1898). (6) Stiller, Harris, Finkelstein, Keresztesy a o d Folkers, THIS J O ~ > R N & I ,68, . 1783 C l O l ( 1 ) . (7) Woollcy (iud Collycr, J . B i d . Cliem.. 169, 2G3 (1945).
C a dpantothenate per tube,
Analoga per tube, Y
Y
0.0 .02 .06 .20 .60 .02 .02 .02 .02 .02
0.0 .0 .0
.O
Lactobacillus arabinosus 17-5, ml.
4.05 9.95 13.90 14.85 14.90 9.82 9.45 9.05 8.05 6.25 4.05 15.40 14.75 12.35 8.90 4 . 0
