Hyaluronidase-catalyzed copolymerization for the single-step synthesis of functionalized hyaluronan derivatives.
Hyaluronidase-catalyzed copolymerization was carried out with monomer combinations of 2-methyl (1a)/2-vinyl (1b), 2-methyl (1a)/2-ethyl (1c), 2-methyl (1a)/2-n-propyl (1d), and 2-vinyl (1b)/2-ethyl (1c) oxazoline derivatives of hyalobiuronate [GlcAbeta(1-->3)GlcN]. All copolymerization reactions proceeded successfully in a regio and stereoselective manner, giving rise to hyaluronan derivatives bearing different N-acyl groups at the C2 position of the glucosamine unit in the polymer chain. The composition of the N-acyl groups was controlled by varying the comonomer feed ratio. The copolymerization mechanism was also discussed.
Ochiai
Hirofumi
H
Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
Ohmae
Masashi
M
Mori
Tomonori
T
Kobayashi
Shiro
S
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D006820:Hyaluronic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006821:Hyaluronoglucosaminidase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013997:Time Factors
D006820:Hyaluronic Acid; D006821:Hyaluronoglucosaminidase