Abstract
When wool is treated in alkaline solutions of sodium thiosulfate, cystine is degraded and at the same time lanthionine is formed. The cleavage of cystine is shown to be partly due to the S-nucleophilic attack of the disulfide bond by the thiosulfate anion, and partly to the effect of the high alkalinity of the solution. The formation of lanthionine is assumed to take place by means of a bimolecular displacement side reaction between the decomposition products of cystine formed by the nucleophile, namely cysteine and cysteinethiosulfonic acid.
Get full access to this article
View all access options for this article.
References
1.
Decroix
G.
Mazingue
G.
, Bull. Inst. Textile France
73 , 41 (1958 ).
2.
Elliott
R. L.
Asquith
R. S.
Hobson
M. A.
, J. Soc. Dyers Colourists
74 , 859 (1958 ); J. Textile Inst. 51, T692 (1960).
3.
Foss
O.
, Acta Chem. Scand . 4 , 866 (1950 ).
4.
Foss
O.
Kringlebotn
I.
, Acta Chem. Scand . 15 , 1608 (1961 ).
5.
Gerthsen
T.
, unpublished investigation.
6.
Golsch
E.
, “Über die alkalische Zersetzung von Cystin,” Ph.D. Thesis, Technische Hochschule Aachen , 1961 .
7.
Greenstein
J. P.
Winitz
M.
, “The Chemistry of the Amino Acids,”
New York , John Wiley and Sons, Inc. , 1961 , p. 2679 .
8.
Kunitz
F. W.
, “Die Rolle der SH-Gruppen für die Lanthioninbildung in Wolle und die irreversible Denaturierung löslicher Proteine,” Ph.D. Thesis Technische Hochschule Aachen , 1960 .
9.
Lees
K.
Elsworth
F. F.
, Proc. Int. Wool Textile Res. Conf., Australia , 1955, C., 363 (1956 ).
10.
Parker
A. J.
Kharasch
N.
, Chem. Rev . 59 , 583 (1959 ).
11.
Schöberl
A.
, Biochem. Z . 313 , 214 (1942 ); Ber. deut. chem. Ges. 76, 970 (1943).
12.
Swan
J. M.
, Angew. Chem . 68 , 215 (1956 ); Nature 179, 965 (1957).
13.
Vassiliadis
A.
Zahn
H.
, J. Soc. Dyers Colourists
78 , 234 (1962 ).
14.
Zahn
H.
Traumann
K.
, Melliand Textilber . 35 , 1069 (1954 ).
15.
Zahn
H.
Kessler
H.
, Makromol. Chem . 27 , 218 (1958 ).
16.
Zahn
H.
Kunitz
F. W.
Hildebrand
D.
, J. Textile Inst . 51 , T740 (1960 ).
17.
Zahn
H.
, Chimia (Aarau)
15 , 378 (1961 ).
18.
Zahn
H.
Gerthsen
T.
Meichelbeck
H.
, Melliand Textilber . 43 , 1179 (1962 ).