Click glycoconjugation of per-azido- and alkynyl-functionalized beta-peptides built from aspartic acid.
Azide- and alkynyl-containing homo-beta(3)-peptides, of up to six residues in length, were synthesised in solution from aspartic acid. Their subsequent conjugation with monosaccharides bearing an azide or a terminal alkyne function was efficiently achieved by copper-mediated cycloadditions leading to two novel families of small glycoclusters. These compounds represent ideal tools to explore carbohydrate-mediated multivalent interactions.
Barra
Marielle
M
Clermont Université, Université Blaise Pascal, Laboratoire SEESIB, BP 10448, F-63000, Clermont-Ferrand, France.
Roy
Olivier
O
Traïkia
Mounir
M
Taillefumier
Claude
C
D000480:Alkynes / Q000737:chemistry*; D001224:Aspartic Acid / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D006020:Glycopeptides; D009842:Oligopeptides; D001224:Aspartic Acid; D003300:Copper