A series of novel haloglycolipids were synthesized based on Cu(i) catalyzed Huisgen's [3 + 2] cycloaddition reaction of diversely functionalized azides and alkynes, using a mixture of N-bromosuccinimide and Cu(i) halide as the halogen source. Since halogen atoms, like bromine and iodine, with a very high scattering power facilitate the solving of crystal structures, the title haloglycolipids could prove to be invaluable in structure-based drug design involving membrane proteins as targets.
Structurally diverse novel glycopeptoids were synthesized which can be attached to biologically important peptides by click reaction to improve their potential to be used in medicinal chemistry. Triazole-linked αβ-hydrid glycopeptoids were synthesized that mimic the conserved linkage region of N-linked glycoproteins in eukaryotes. The amide bonds were replaced with triazole rings, and αβ-hybrid peptoids were introduced as the backbone modification in peptidomimetics. In addition to their facile synthesis, these modifications have the possibility of introducing otherwise impossible conformations in the peptide backbone.
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