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By Jesse P. Greenstein and Alexander Haddow

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D From titration data. From quantity of dinitrophenyllysine formed on treatment with dinitrotluorobenzene. I Titration data could not be evaluated since introduced basic groups interfere. Reaction between nitrogen mustards and protein carboxyl groups cannot readily be detected from changes in acid combination since the titration of ‘the mustard amine to its salt and the back titration of the carboxyl ion with acid occur in the same pH range. There is no reason to believe that the nitrogen mustard esters derived from proteins are exceptionally THE REACTIONS O F CARCINOGENS WITH MACROMOLECULES 39 labile since Davis and Ross (1950) found that the acetates of both aliphatic and aromatic mustards were more stable to acid hydrolyses and only slightly less stable to alkaline hydrolysis than ethyl acetate.

The primary reactions which are generally accepted are + + OH + H+ + e HzO + HrOf e HzO+-+ OH H+ HzO-, and there is abundant evidence for the existence of the reactive OH radical. The reaction of the low-energy'"ejected electron (the thermal electron) is generally thought1to result inthe formation of H atoms by a reaction which may be of this type. O + e-+ H + OH- It should, however, be stressed that there is no direct experimental evidence for an H atom and a number of experiments (cf. Dainton, 1952) contraindicate its formation in this way.

CH2)2Cl, convincing explanation would seem to be that the “combined” chlorine is present as a ‘ I gegen-ion ” necessary for maintaining electrical neutrality of the protein after esterification of carboxyl groups. , not far from the isoelectric point) the majority of the acid and basic groups are internally neutralized and after treatment with mustard gas the chloride ion split off will form a salt with the ammonium ion: Protein-COOProtein-COOR + . - . HaN-Protein 1+RCI (mustard gas) . Hs&-Protein c1- On extraction with water the chloride ion will exchange slowly with hydroxyl ions and this could account for the “hydrolysis” observed by Peters and Wakelin (1947).

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