Syntheses of heparin - like pentamers containing “opened” uronic acid moieties

Synthetic Oligosaccharides as Heparin-Mimetics Displaying Anticoagulant Properties

“…A flexible acyclic residue was used to replace either glucuronic acid (E) (9) or iduronic acid (G) (10) in the ABD (Fig. 6) [26]. The results of bioassay clearly demonstrated that residue E should be rigid while residue G should be flexible, consistent with previous studies [27][28][29][30][31][32].…”

“…The importance of the uronic acid moieties in the ABD is another feature that has been intensively studied [26]. Conformational studies have shown the presence of the conformational equilibrium of 4 C 1 , 1 C 4 , and 2 S O conformers at L-iduronic acid residue [27][28][29][30][31][32].…”

Synthesis and Biological Evaluation of a Heparin‐Like Hexasaccharide with the Structural Motifs for Binding to FGF and FGFR

“…The removal of methoxycarbonyl and acyl groups was performed with lithium hydroperoxide and then aqueous/alcoholic potassium hydroxide in order to minimise elimination. [29,30] The resulting partially protected hexasaccharide 23 was sulfated by treatment with SO 3 ·Py complex in pyridine. Close monitoring by TLC revealed that a mixture of partially O-sulfated products was obtained after stirring for 24 h. It was necessary to purify that mixture by Sephadex LH-20 chromatography and to treat the resulting residue with fresh SO 3 ·Py complex in order to complete O-sulfation and to isolate pure 24 (50 %).…”

“…[20] Finally, hydrogenolytic cleavage of the benzyl groups and simultaneous reduction of the azido groups in 24, followed by selective N-sulfation, yielded compound 2 (93 %), which was purified by gel permeation chromatography by the protocol previously reported for heparin-like oligosaccharides. [30] The 1 H and 13 C NMR spectra of hexasaccharide 2 were fully assigned by conventional 1D and 2D spectroscopy (Table 1). These assignments were carried out by identification of the spin systems of the residues and further connections based on interresidue NOE.…”

From Polymer to Size‐Defined Oligomers: An Expeditious Route for the Preparation of Chondroitin Oligosaccharides

“…Further coupling of 18 with imidate 6 or 16 under the same conditions gave hexasaccharide derivatives 19 and 20, respectively, in 65 % yield. Deprotection of 19 was achieved through transformation of the N-trichloroacetyl groups into their N-acetyl congeners by radical reduction with tributylstannane [8] followed by a two-step saponification with lithium hydroperoxide [16] and sodium hydroxide, to give the target hexasaccharide glycoside 21 in good yield. Thus, an efficient route is now open for the preparation of size-defined chondroitin oligomers containing a fluorescent glycoside as useful probes for the study of the biosynthesis as well as the polymerization of chondroitin sulfate chains.…”