The Specificity of Certain Phosphine Derivatives as Reducing Agents for the Disulfide Bond in Wool Keratin

Abstract

It is suggested that, while the phosphine derivatives tetrakis-hydroxymethyl phos phonium chloride and tris-diethylaminomethyl phosphine can readily reduce disulfide to thiol in wool, they also lead to the formation of some monosulfide (lanthionine) in hydrolyzates of wool samples, together with what is apparently thiohemiacetal (—SCH2OH) in the intact wool. Furthermore, examination of hydrolyzates of these reduced wool samples reveals probable modification of lysyl, tyrosyl, prolyl, and histidyl residues. These observations must limit the use of these reagents in cases where specific modifications of proteins are required.