ChemInform Abstract: Diethylene and Triethylene Glycol Spacers for the Preparation of Neoglycoproteins.

Selectivity among Two Lectins: Probing the Effect of Topology, Multivalency and Flexibility of “Clicked” Multivalent Glycoclusters

“…A better protocol for this process is now under investigation in our group. The CuAAC of the propargylated scaffold 13 with A [40,48] provided the desired glycoconjugate 14 and deprotection of the acetates afforded the hydroxylated hexavalent glycocluster 15. In the case of the hexapropargylated calixarene 13, only one signal is observed for tBu (d = 0.81 ppm), ArH (d = 7.15 ppm) and the bridging methylene protons (d % 4 ppm).…”

“…The acetylated glycoconjugate 11 was then obtained by conjugation with the carbohydrate derivative A [40,48] and unmasking of the hydroxyl groups gave the desired glycocluster 12. As attested by the 1 H and 13 C NMR spectra, calixarenes 11 and 12 adopt the same flattened cone conformation.…”

“…The NMR spectroscopic analyses of the mixtures obtained provided non-exploitable data due to the presence of copper ions in the porphyrin. We then tried a series of "click" chemistry conditions by using different sources of Cu I for the conjugation of the non-metallated porphyrin 17 with the carbohydrate probe A [40,48] (Table 1). Since the metallation of the porphyrin was the main problem observed, we have selected triphenylphosphine-Cu I complexes, which have been described recently to be more selective in CuAAC.…”

“…We focused here on the synthesis of the tetravalent linear and cyclic oligomers and their conjugation to a carbohydrate probe through "click" chemistry. [45][46][47] The secondary amine of the linear tetrapropargylated b-peptoid 1 [44] was acetylated and the corresponding acetamide 2 was then conjugated to 1-azido-3,6-dioxaoct-8-yl-2,3,4,6-tetra-O-acetyl-b-d-galactopyranoside A [40,48] through CuAAC under microwave irradiation to afford the peracetylated glycoconjugate 3 (Scheme 1). Saponification of both the tert-butyl ester and acetates afforded the hydroxylated glycocluster 4.…”

Design of Triazole‐Tethered Glycoclusters Exhibiting Three Different Spatial Arrangements and Comparative Study of their Affinities towards PA‐IL and RCA 120 by Using a DNA‐Based Glycoarray

“…Detritylation was performed with DCA in CH 2 [11] units were coupled according to the phosphoramidite elongation cycle (see above), and this was followed by the first three nucleotides. Solid-supported DMTr-A bz G ibu C bz decaalkyne derivative (0.6 mmol) was transferred into a microwave vial, and 1-azido-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-b-d-galactopyranoside [12,44] (30 mmol, 15.2 mg, in 100 mL of methanol), CuSO 4 (1.2 mmol, 6 mL of 200 mm water solution) and sodium ascorbate (6 mmol, 24 mL of 250 mm water solution) were added. The sealed vial was irradiated with microwaves for 20 min at 60 8C with magnetic stirring.…”