Spatial Screening of Cyclic Neoglycopeptides: Identification of Multivalent Wheat Germ Agglutinin Ligands**
نویسندگان
چکیده
General. Solid-phase peptide synthesis was carried out in plastic syringe reactors. Fmocprotected amino acids were obtained from Novabiochem (Läufelfingen, Switzerland) or prepared according to standard procedures. Bovine serum albumin (A7638), biotinylated WGA (L5142), alkaline phosphatase-coupled monoclonal anti biotin antibody (A6561), BCIP/NBT tablets (B5655), peroxidase-labeled WGA (L7017), and porcine stomach mucin type III (M1778) were obtained from Sigma. Compound numbers used within this supporting information are the same as in the printed article.
منابع مشابه
Mechanistic Insight into Nanomolar Binding of Multivalent Neoglycopeptides to Wheat Germ Agglutinin.
Multivalent carbohydrate-protein interactions are frequently involved in essential biological recognition processes. Accordingly, multivalency is often also exploited for the design of high-affinity lectin ligands aimed at the inhibition of such processes. In a previous study (D. Schwefel et al., J. Am. Chem. Soc. 2010, 132, 8704-8719) we identified a tetravalent cyclopeptide-based ligand with ...
متن کاملSpatial screening of cyclic neoglycopeptides: identification of polyvalent wheat-germ agglutinin ligands.
Natural and synthetic polyvalent ligands can act as inhibitors of biological processes or as effectors of signal-transduction pathways. 2] In the case of carbohydrate–lectin interactions, polyvalency is of particular importance because individual carbohydrate epitopes are usually bound with only weak affinity and often broad specificity. The potency of a polyvalent inhibitor depends on the spat...
متن کاملOn-bead synthesis and binding assay of chemoselectively template-assembled multivalent neoglycopeptides.
The investigation of recognition events between carbohydrates and proteins, especially the control of how spatial factors and binding avidity are correlated in, remains a great interest for glycomics. Therefore, the development of efficient methods for the rapid evaluation of new ligands such as multivalent glycoconjugates is essential for diverse diagnostic or therapeutic applications. In this...
متن کاملTemporary attachment of carbohydrates to cyclopeptide templates : a new strategy for single-bead analysis of multivalent neoglycopeptides
Employing a cleavable carbohydrate–peptide linker, a new strategy for single-bead analysis of multivalent cyclic neoglycopeptides based on Edman degradation is described. Edman degradation of glycopeptides is hampered by the acid lability of the glycosidic bond and potential incompatibilities of phenylthiohydantoin (PTH) derivatives of glycosylated amino acids with PTH derivatives of the protei...
متن کاملHigh-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction
A series of six mono-, di-, and trivalent N,N'-diacetylchitobiose derivatives was conveniently prepared by employing a one-pot procedure for Cu(II)-catalyzed diazo transfer and Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) starting from commercially available amines. These glycoclusters were probed for their binding potencies to the plant lectin wheat germ agglutinin (WGA) from Triticum vu...
متن کامل