Synthesis of glycosaminoglycans via enzymatic polymerization |
| |
Authors: | Shiro Kobayashi Ryosuke Itoh Hidekazu Morii Shun-Ichi Fujikawa Shunsaku Kimura Masashi Ohmae |
| |
Institution: | Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan |
| |
Abstract: | Hyaluronic acid and chondroitin were successfully synthesized as representative molecules of glucosaminoglycans and galactosaminoglycans found in a glycosaminoglycan family via enzymatic polymerization catalyzed by testicular hyaluronidases. A newly designed N-acetylhyalobiuronate oxazoline derivative with a β-D -glucuronyl-(1→3)-N-acetyl-D -glucosamine disaccharide structure served as a transition-state analogue substrate monomer for the enzyme, giving rise to artificial hyaluronic acid in 52% yields with a number-average molecular weight of 1.35 × 104 through ring-opening polyaddition in a perfect regioselective and stereoselective manner. A novel N-acetylchondrosine oxazoline derivative with a β-D -glucuronyl-(1→3)-N-acetyl-D -galactosamine disaccharide structure also acted as a transition-state analogue substrate monomer for the enzyme, yielding artificial chondroitin in 35% yields with a number-average molecular weight of 2.5 × 103. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 3541–3548, 2003 |
| |
Keywords: | enzymatic polymerization glycosaminoglycans hyaluronic acid chondroitin testicular hyaluronidases enzymes polysaccharides ring-opening polymerization |
|
|