Conformational changes and anticoagulant activity of chondroitin sulfate following its O-sulfonation

Pattern‐Based Recognition of Heparin Contaminants by an Array of Self‐Assembling Fluorescent Receptors

“…[2] Even though some batches of heparin were found to contain up to a third of this non-natural form of chondroitin sulfate, its presence was masked in standard quality-control assays owing to the inherent anticoagulant activity of OSCS. [3] The development of quick and reliable tests for heparin contaminants is currently of great interest. [4] Herein we report the design and evaluation of a fluorescent receptor array that is able to assess the quality of a heparin sample by quickly differentiating UFH from OSCS and other commonly encountered negatively charged polymers.…”

Solvolytic depolymerization of chondroitin and dermatan sulfates

“…c in the spectrum of fraction dp 6 are H-1 of methyl 2-acetamido-2-deoxy-D-galactofuranoside, ÀCOOCH 3 of glucuronate at the reducing end, and -OCH 3 of methyl 2-acetamido-2-deoxy-D-galactofuranoside. 1 H NMR analysis of oligosaccharides (dp [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] showed that each fraction was remarkably pure having a single major component (Fig. 3).…”

“…15,16 These per-O-sulfonated chondroitin oligosaccharides were compared to per-O-sulfonated chondroitin polymer, which has been detected as a contaminant in low-molecularweight heparin 17 and has been shown to give rise to its serious toxicity. 18 These products were also compared to those of hyaluronan derivatives (Tables 1 and 2).…”

“…15,16 This method was slightly improved for CS oligosaccharides in this paper. To obtain the tributylamine (TBA) salt of the oligosaccharides, 50 lL of TBA was added to each size-uniformed CS oligosaccharide sample (1.0 mg) in 1.0 mL of distilled water adjusted to pH 2.8 with 0.1 M HCl.…”

Semi‐Synthesis of Unusual Chondroitin Sulfate Polysaccharides Containing GlcA(3‐O‐sulfate) or GlcA(2,3‐di‐O‐sulfate) Units

“…In particular, the synthesis of unnatural per-O-sulfated CS has been accomplished in one step from bovine tracheal cartilage CS, [4] and this product was recently identified as a contaminant of heparin lots, to which it had been added to fraudulently increase the anticoagulant titer of the preparation. [5] To the best of our knowledge, only one report has appeared in the literature regarding the direct partial sulfation of CS, and this approach yielded a randomly sulfated polysaccharide of very high structural heterogeneity.…”