On the reaction of N-acetylchondrosine, N-acetylchondrosine 6-sulfate, chondroitin 6-sulfate, and heparin with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

Add time:08/10/2019    Source:sciencedirect.com

N-Acetylchondrosine was activated at pH 4.75 with excess 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to give an O-acylisourea that consists of equimolar amounts of N-acetylchondrosine and 1-(3-dimethylaminopropyl)-3-ethylurea, with concomitant uptake of 0.94 mol of hydrogen ion per mol of N-acetylchondrosine. The product was treated with sodium borohydride to give a carboxyl-reduced disaccharide, but it did not react with a nucleophile reagent, such as glycine ethyl ester, over the pH range of 4.75–11.0. The O-acylisourea was hydrolyzed mostly into N-acetylchondrosine and 1-(3-dimethylaminopropyl)-3-ethylurea with 0.1m sodium carbonate overnight at room temperature, but a small proportion was transformed into the N-acylurea. N-Acetylchondrosine 6-sulfate, chondroitin 6-sulfate, and heparin were also activated at pH 4.75 with excess 1-(3-dimehtylaminopropyl)-3-ethylcarbodiimide hydrochloride to give the corresponding O-acylisoureas containing one mol of 1-(3-dimethylaminopropyl)-3-ethylurea moiety per mol of uronic acid residue, respectively.

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