Zusammenfassung
Die früher als «Cystinmonosulfoxyd» beschriebene Verbindung (Thiosulfinat II) verhält sich wie eine äquimolekulare Mischung von Cystin (I) und dem entsprechenden Thiosulfonat (III). Oxydation von Cystin mit Perameisensäure führt, besonders in Gegenwart von HCl, über die Zwischenprodukte Thiosulfonat (III) und Sulfinsäure (VI) zu Cysteinsäure (VII).
Literatur
L. Young andG. A. Maw,The Metabolism of Sulphur Compounds, Chapter V (Methuen, London 1958).
J. A. Maclaren, S. J. Leach, andI. J. O'Donnell, Biochim. biophys. Acta35, 280 (1959).
J. A. Maclaren, S. J. Leach, andJ. M. Swan, J. Text. Inst.51, T 665 (1960).
G. Toennies andT. F. Lavine, J. biol. Chem.113, 571 (1936).
R. Emilliozi andL. Pichat, Bull. Soc. chim. Fr.1959, 1887.
B. J. Sweetman, Nature (Lond.)183, 744 (1959) has shown that this substance has the thiolsulfonate structure (III) and not the ‘disulfoxide’ structure ofToennies andLavine 4.
T. F. Lavine, J. biol. Chem.113, 583 (1936).
G. Toennies, J. Amer. chem. Soc.56, 2198 (1934).
H. Gräfje, Diplomarbeit Giessen (1955) and private communication.
G. Toennies andT. F. Lavine, J. biol. Chem.105, 107 (1934).
G. Toennies, J. biol. Chem.122, 27 (1937–1938).
G. E. Utzinger, Exper.16, 136 (1960).
This combination of techniques was suggested byDr. W. E. Savige of this laboratory. The solvent used was the mixture ‘P’ ofT. L. Hardy, D. O. Holland, andJ. H. C. Naylor, Analyt. Chem.27, 971 (1955).
W. Stricks, I. M. Kolthoff, andN. Tanaka, Analyt. Chem.26, 299 (1954).
Kindly determined by Dr.W. F. Forbes of this laboratory using an IR 7 Beckman spectrophotometer.
H. J. Backer andH. Kloosterziel, Rec. Trav. chim. Pays-Bas73, 129 (1954).
A. Schöberl andH. Gräfje, Proc. Int. Wool Text. Res. Conf. Aust. 1955C, 157 (1956).
Separate studies showed that VI may be an indirect product formed by hydrolysis of III.
H. Bredereck, A. Wagner, H. Beck, andR. J. Klein, Chem. Ber.93, 2736 (1960).
For a recent review seeHouben-Weyl,Methoden der Organischen Chemie, 4. Aufl., vol. 9 (Georg Thieme, Stuttgart 1955).
G. Toennies andJ. J. Kolb, Nature (Lond.)177, 281 (1956).
D. Barnard andE. J. Percy, Chem. and Ind.1960, 1332.
Grateful acknowledgements are due to Dr.G. E. Utzinger for a sample of the ‘monosulfoxide’ for comparison purposes.
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Maclaren, J.A. ‘Cystine monosulfoxide’ and related compounds. Experientia 17, 346–347 (1961). https://doi.org/10.1007/BF02201752
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DOI: https://doi.org/10.1007/BF02201752