title: Synthesis of multivalent neoglyconjugates of MUC1 by the conjugation of carbohydrate-centered, triazole-linked glycoclusters to MUC1 peptides using click chemistry.
abstract: The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GlcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GlcNAc-centered neoglycoclusters were assembled by reaction of a GlcNAc core containing peripheral propargyl functionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Dong Jun
authors.initials: DJ
authors.lastname: Lee
authors.forename: Sung-Hyun
authors.initials: SH
authors.lastname: Yang
authors.forename: Geoffrey M
authors.initials: GM
authors.lastname: Williams
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D006001:Glycoconjugates / Q000737:chemistry*; D008968:Molecular Conformation; D018396:Mucin-1 / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D002241:Carbohydrates; D006001:Glycoconjugates; D018396:Mucin-1; D010455:Peptides; D014230:Triazoles; D003300:Copper