NOTES
4028
VOl. 73
'LABLE 1 CAKBOBEXZOXY LYSINETRIPEPrIDE DERIVATIVES
Molecular formula
Compounds
Nitrogen, "/o Calcd. Found
M p , T
(cor 1
Mol. wt
Carbobenzoxy tripeptide esters Z.Gly-Z.Lys-Gly.0B~(L) c LJlijaosh 4 618.7 C j J I ~ " 0 ~ S ~ 584.7 Z.Ala-Z.Lys-Ala.OEt ( 3j ~ Z.Ala-Z.Lys-Ala.OBz ( 3 ~ ) C,&:O8Np 646.7 2.Ala-Z.Lys-Ala.OBz ( L-D-L) C&~AO~T\'.I 646 7 ZAla-Z.Lys-Ala.OBz (L-D-D) C35HteOdNc 646 i CalHo4Oi2;Sc 953 1 Z2.Lys-Z.Lys-%Lys.OMe ( 3 ~ ) c ,7HSSOl s,, 7029 2 Z9.Lys-Z LYS-Z.LYS.OBL (3~) CS7H6sOlLKG 1029 L! Z,.Lys-Z.Lys-Z.Lys.OBz (L-D-L) C S ~ H ~ ~ O E S ~ 1029 , 2 Zz.Lys-Z.Lys-Z.Lys~OBz(L-D-D)
120-132 191-192 183-184 160-161 173-174 143- 145 153-154 141-142 151-152
I
9.1 9.6 8.7 8.7 8.7 8.8
9.2 9.7 8.7 8.8 8.8 8.8 8.3 8.3 8.3
8.2
8.2 8.2
Carbobenzoxy tripeptide hydrazide CtsH,vjOiSs 570.6 208 14.7 14.6 10 Z.Ala-Z.Lys-Ala.NHNH2 ( 3 ~ ) a The following abbreviations are used (cf. ref. 2, 3, Table I, footnote a): 2 : carbobenzoxy, C ~ H S C H ~ O C OGly: ; SH(CH2)CO; Ala: NH(CHCH3)CO; Lys: NH(CHC4HsSHJCO; peptide linkage indicated by hyphen; Me: CH,; E t : C2Hs; Bz: CJ-€&HZ; configuration follows compound in parentheses. E.g., a,€-dicarbobenzoxy-L-lysyl-a-carbobenzoxy-D-lysyl-e-carbobenzoxy-L-lysine benzyl ester : Z?.I.yq-%.I,ys-%.LysOBz(I.-D-I.) ; L-alanyl-D-lysyl-D-alaninemonohydrochloride: H.Ala-Lys-Ala.OH.HC1 (L-D-D). T A B L E I1 LYSINETRIPEPTIDES: ANALYTICAL DATAAXD SPECIFICKUTATION IN 0.5 *V HCl (BASIS: FREEPEPTIDES) NO.
11
12 13 14 15 16 17
Compound" H*Gly-Lys-Gly.OH.HCI (I.) H-Ala-Lys-Ala-OH.HC1 ( 3 ~ ) H.Ala-Lys-Ala.OH-HC1 (L-D-L) H.Ala-Lys-AlwOH.HC1 (L.I)-u) H.Lys-Lys-Lys.OH.aHC1 ( 3 ~ ) H*Lys-Lys-Lys*OH*3HCl(L-D-L' H*Lys-Lys-Lys.OH*3HCI(r..u-u!
Mo1e c u1ar formula
Mol. wt. C ~ o l t ~ 0 0 4 S ~ ~ H C219 t i . Y C:zHzrOiNi.HCI 324.8 C~ZHZ~~~N'.HC :324. I R C~IKE~APU'~.€ICIX24.8 C:~HiaO&~~3IICI Ti 11 .O C I ~ H S ~ O O T V ~ H C:t II 1 . 9 CiaHasO4Ns.3lICI 51 1 . $1
Nitrogen, % Amino N, % HCl, % Neut. equiv.6 Calcd. Found Cslcd. Found Calcd. Found Calcd. Found 18
'
',I
l%(i
..
..
10.9
10 . Cottle. c1 ai.,J . Oug. Chein., 11, 286 (1946). G. Rieveschl, Jr.. and 0. M. Gruhzit, Federation Pvoc., 4, 150 (1945): ( 5 ) H.Gilman and F. Schulze, THISJOURNAL, 47, 2002 (1925). f G ) H. Bohme, Bev., 70, 379 f1937). E. R. Loew, et ai., J . P h a v m a c ~ l . ,83, 120 (1945); and E. R. Loew, (7) Prepared by the procedure of C . F. H. Allen and S. Converse, Phvsiol Reos., 27, 642 (1947). In certain other antihistaminic types, "Organic Syntheses," Coll. Vol I. John Wiley a n d Sons, Inc., New R. E IIamlin, rf a i . , THISJOUKNAL, 71, 2731 (1949), the introduction of ii p-chlorophenyl group was found t o enhance t h e activity. 111 Tork. N. Y..1946. p. 226 this rrgard, t h e syrithesi.; o f 2-phenyl-2-0 c h l o r o p h e r i v l - 4 - r n e t . h ~ l r n ~ r - (81 Obtained by the method of H. Bijhme, O V R .S y n t h e s e s , 20, 7(1 I 9 . k O l . and the modifications of (> B I 3 a c h m m : i n d D E . Cooper. pholine i.; i n piugrr..s !* , 4. f i ' h r m . . 9, 302 (19441
,
