"Click" saccharide/beta-lactam hybrids for lectin inhibition.
Hybrid glycopeptide beta-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "click" cycloaddition reaction, and as shown by NMR/MD experiments, binding of the resulting mimetics to Ulex Europaeus Lectin-1 (UEL-1) occurred after a "bent-to-extended" conformational change around a partially rotatable triazolylmethylene moiety.
Palomo
Claudio
C
Departamento de Química Orgánica-I, Universidad del País Vasco, Joxe Mari Korta R& D Center, San Sebastián, Spain.
Aizpurua
Jesus M
JM
Balentová
Eva
E
Azcune
Itxaso
I
Santos
J Ignacio
JI
Jiménez-Barbero
Jesús
J
Cañada
Javier
J
Miranda
José Ignacio
JI
D040761:Biomimetic Materials / Q000737:chemistry / Q000494:pharmacology; D006020:Glycopeptides / Q000737:chemistry* / Q000494:pharmacology*; D037102:Lectins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D010940:Plant Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry; D011487:Protein Conformation; D039762:Ulex / Q000737:chemistry; D047090:beta-Lactams / Q000737:chemistry* / Q000494:pharmacology*
D006020:Glycopeptides; D037102:Lectins; D010940:Plant Proteins; D047090:beta-Lactams