Yariv reagents are glycosylated triphenylazo dyes, some of which bind to the polysaccharide component of arabinogalactan proteins (AGPs), proteoglycans found in plant cell walls. However, the exact reason for the selectivity in the presence/absence of AGP binding ability among Yarivs remains unknown. The Yariv reagents are known to form supramolecular aggregates in solution. We use circular dichroism to show that the Yariv reagent aggregates possess helical chirality, and the AGP binding ability of the Yariv reagents is correlated to its helical chirality.
Yariv reagents are glycosylated triphenylazo dyes, some of which bind to the polysaccharide component of arabinogalactan proteins (AGPs), proteoglycans found in plant cell walls. However, the exact reason for the selectivity in the presence/absence of AGP binding ability among Yarivs remains unknown. The Yariv reagents are known to form supramolecular aggregates in solution. We use circular dichroism to show that the Yariv reagent aggregates possess helical chirality, and the AGP binding ability of the Yariv reagents is correlated to its helical chirality.
Two bench-stable and readily accessible pyrene-based diaryne precursors based on triflate as well as TMS triflate motifs are introduced and compared in their [4+2]-Diels–Alder reactions with tetracyclone to give an oligophenyl-substituted dibenzo[e,l]pyrene in both cases. By single-crystal X-ray analysis, this twistacene showed helical chirality and an end-to-end contortion of 49.6° due to steric repulsion.
The Chirality of Yariv Reagent Aggregates Correlates with AGP–binding Ability
