Tailored chondroitin sulfate glycomimetics via a tunable multivalent scaffold for potentiating NGF/TrkA-induced neurogenesis† †Electronic supplementary information (ESI) available: Detailed synthesis of CS disaccharides including 1H, 13C NMR, and mass data, general peptide synthesis, click reaction including FT-IR spectra of polyprolines and glycopeptides, procedures for CD measurements including spectra of glycopeptide 1–7, ELISA and SPR measurements including complete kinetic parameters, computational methods including predicted glycopeptide binding sites on the NGF/TrkA complex in table, cellular assays and immunohistochemistry are described. See DOI: 10.1039/c4sc02553a Click here for additional data file.

General Methods Unless otherwise stated, reactions were performed in flame-dried glassware under argon atmosphere and using anhydrous solvents. All commercially obtained reagents were used as received unless otherwise noted. Thin layer chromatography (TLC) was performed using E. Merck silica gel 60 F254 precoated plates (0.25 mm). Visualization of the developed chromatogram was performed by UV, cerium ammonium molybdate or ninhydrin stain as necessary. Merck silica gel 60 (particle size 0.040 0.063 mm) was used for flash chromatography. Gel filtration chromatography (Sephadex G-15 ultrafine) was used in order to achieve purification of the glycopeptides. 1H NMR and proton decoupling experiments were recorded on a Bruker AVIII 400 (400 MHz) spectrometer and are reported in parts per million (δ) relative to CDCl3 (7.26 ppm), CD3OD (4.87 ppm), and D2O (4.80 ppm). Data for the 1H NMR spectra are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, bs = broad singlet, d = doublet, t = triplet, q = quartet, m = multiplet), coupling constant in Hz, and integration. 13C NMR spectra were obtained on a Bruker AVIII 400 (100 MHz) spectrometer and are reported in terms of chemical shift. Mass spectra were obtained from Chemical, Molecular and Materials Analysis Centre at the National University of Singapore.