Novel Cross-linking Compounds Formed through the Reaction of N^α-Acetyltryptophan with Hexanal

Abstract

We separated three N^α-acetyltryptophan (Ac-Trp) derivatives formed through the reaction of Ac-Trp with hexanal, which is a major secondary product of lipid peroxidation. They were identified as 1-[N¹-(N^α-acetyltryptophano)]-1-(N^α-acetyltryptophan-2-yl)hexane (Trp-HL-1), 1, 1-bis[N¹-(N^α-aacetyltryptophano)]hexane (Trp-HL-2) and 1, 1-bis(N^α-acetyltryptophan-2-yl)hexane (Trp-HL-3). Hexanal became a cross-linker between two Ac-Trp molecules on the formation of these compounds. Since Trp-HL-1 contained a newly formed asymmetric carbon atom, its diastereomers, Trp-HL-1a and Trp-HL-1b, were separated and characterized by ORD.