By J. Greenstein, et al.,
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Young et al. (1947) record that zein and gliadin failed to combine, while keratin and salmine reacted with mustard gas. Reaction with salmine is surprising since the only reactive side chains are those of arginine which would not be expected to react a t pH 7 to 8; however, the molecular weight of this protein is low so that the total amount of mustard gas combined (55 mg. per gram of protein) could be accounted for by reaction with terminal carboxyl and amino groups. THE REACTIONS OF CARCINOGENS WITH MACROMOLECULES 35 The esters derived from carboxyl groups in proteins are very labile; thus Alexander et al.
The shift in the isoelectric point of egg albumin from pH 5 to 8 on treatment with propylene oxide noted by Fraenkel-Conrat (1944) could result from the blocking of approximately 10 % of the carboxyl groups and could also have been brought about by the quaternization of the imidazole group of histidine, which was shown to occur with mustard gas (Davies and Ross, 1947) ; it does not therefore provide confirmatory evidence for extensive reaction with the carboxyl groups. The limited amount of valid data indicates that epoxides in general do not react extensively with carboxyl groups of proteins near their isoelectric point except for epichlorhydrin, which can react with up to 40% of the carboxyl groups in wool.
Variations of this order have been observed for polymers the molecular weight of which does not exceed a few hundred thousand and show clearly that orientation of the molecules is not sufficient to explain the magnitude of the anomaly found with molecules such as DNA for which a different mechanism must be operative. A number of naturally occurring macromolecules such as tobacco mosaic virus, hyaluronic acid, fibrinogen and myosin, and the cytoplasmic protein of algae have similar viscosity characteristics.