Synthesis of end-functionalized glycopolymers containing α(2,8) disialic acids via π-allyl nickel catalyzed coordinating polymerization and their interaction with Siglec-7.

An allene monomer containing an α(2,8) disialic acid was polymerized by a π-allyl nickel complex with an azido group to produce end-functional glycopolymers with an excellent polydispersity index. The polymers allowed terminal modification with a fluorescent dye by click chemistry. The glycopolymers can dissociate Siglec-7-GD3 interactions at low concentrations.

The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect.

The synthesis of α-sialosides is one of the most difficult reactions in carbohydrate chemistry and is considered to be both a thermodynamically and kinetically disfavored process. The use of acetonitrile as a solvent is an effective solution for the α-selective glycosidation of N-acetyl sialic acids. In this report, we report on the α-glycosidation of partially unprotected N-acetyl and N-glycolyl donors in the absence of a nitrile solvent effect.