Specific pupylation as IDEntity reporter (SPIDER) for the identification of protein-biomolecule interactions.

Protein-biomolecule interactions play pivotal roles in almost all biological processes. For a biomolecule of interest, the identification of the interacting protein(s) is essential. For this need, although many assays are available, highly robust and reliable methods are always desired.

Single-wing extended tribenzotriquinacenes via bowl-shaped dehydrobenzene and isobenzofuran tribenzotriquinacene derivatives.

Monoaryne and monoisobenzofuran analogues of a C(3v)-symmetrical tribenzotriquinacene (TBTQ) were generated in situ and trapped with various dienes and dienophiles, respectively. In this way, a series of single-wing extended TBTQ derivatives bearing the bowl-shaped TBTQ unit in different topographical expositions have become accessible. This includes some novel tribenzotriquinacene "dimers", in which two TBTQ bowls are attached in syn- or anti-orientation at the terminal positions of rigid linker units.

Tribenzotriquinacenes based on regioselective bis-formylation: optical resolution and absolute configuration of inherently chiral derivatives and synthesis of the first cyclophane-type tribenzotriquinacene dimers.

Enantiomerically pure tribenzotriquinacenes (TBTQs) bearing two monofunctionalized aromatic nuclei were synthesized for the first time and their optical properties and absolute configuration determined. A remarkably regioselective bis-formylation of the fully bridgehead methylated parent TBTQ hydrocarbon with MeOCHCl(2)/TiCl(4) afforded a mixture of two C(s)-symmetrical (achiral) difunctionalized derivatives together with one C(1)-symmetrical (chiral) isomer. Reduction and subsequent column chromatography furnished the three respective benzylic TBTQ dialcohols.

Synthesis and optical resolution of inherently chiral difunctionalized tribenzotriquinacenes.

The synthesis of several inherently chiral tribenzotriquinacenes (TBTQs) bearing one single mono- or difunctionalized aromatic nucleus and the optical resolution of one of these derivatives, a TBTQ-based salicylic acid (11), are described for the first time. Efficient access to enantiopure, inherently chiral tribenzotriquinacenes may lay a foundation for studies of novel container compounds, supramolecular aggregation, chiral recognition, and asymmetric catalysis.