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

✍ Scribed by Yuko Inoue; Kinzo Nagasawa

• Book ID: 102990997
• Publisher: Elsevier Science
• Year: 1982
• Tongue: English
• Weight: 959 KB
• Volume: 111
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(82)85012-x

✦ Synopsis

N-Acetylchondrosine was activated at pH 4.75 with excess I-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to give an 0-acylisourea that consists of equimolar amounts of N-acetylchondrosine and I-(3-dimethylaminopropyl)-3-ethylurea, with concomitant uptake of 0.94 mol of hydrogen ion per mol of iV-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-l 1.0. The O-acylisourea was hydrolyzed mostly into N-acetylchondrosine and l-(3-dimethylaminopropyl)-3-ethylurea with 0.1~ 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 I-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to give the corresponding O-acylisoureas containing one mol of I-(3-dimethylaminopropyl)-3-ethylurea moiety per mol of uranic acid residue, respectively.