Isolation of γ -L-glutaminyl 4-Hydroxybenzene and γ -L-glutaminyl 3,4-Benzoquinone: A Natural Sulfhydryl Reagent, from Sporulating Gill Tissue of the Mushroom Agaricus bisporus

Early in the development of spores, there appears in gill tissue of the mushroom Agaricus bisporus a red pigment that inhibits mitochondrial respiration. The inhibitor and its immediate precursor were isolated from the mushroom and identified as γ-L-glutaminyl 3,4-benzoquinone (I) and γ-L-glutaminyl 4-hydroxybenzene (II), respectively, neither of which had previously been described. II was synthesized chemically and the synthetic material was identical with isolated II in all regards. An enzyme that oxidizes II to I was isolated concurrently. I reacts unusually rapidly, completely, and at low concentration with the sulfhydryl groups of various mitochondrial enzymes, accounting for its originally observed properties. It may also prove of value as a general inhibitor of sulfhydryl-dependent enzymes.