Synthesis and reactivity of phenolic systems conjugated with sulfhydrylic compounds

Conjugates of phenols with biological thiols have recently received increasing interest because of their peculiar properties in most cases enhanced or significantly modified with respect to the parent phenols. Main focus of the research activity developed in this PhD work was the chemistry of thioalkyl conjugates of catechols. Among these cysteinyldopas, mainly the 5S and 2S isomers, that are produced by epidermal melanocytes of man and other mammals and are involved in the biosynthesis of pheomelanins, the characteristic pigments of red hair, commonly implicated in the abnormal susceptibility of red haired fair complexioned individuals to sunburn and skin cancer. Overall the results of this work have greatly contributed to the definition of the structure, biosynthesis and functional significance of pheomelanins.