Hyaluronidase-catalyzed copolymerization for the single-step synthesis of functionalized hyaluronan derivatives

Biomacromolecules. 2007 Apr;8(4):1327-32. doi: 10.1021/bm061136d. Epub 2007 Mar 23.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Catalysis
  • Hyaluronic Acid / analogs & derivatives*
  • Hyaluronic Acid / chemical synthesis*
  • Hyaluronic Acid / chemistry
  • Hyaluronoglucosaminidase / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Sequence Data
  • Sensitivity and Specificity
  • Stereoisomerism
  • Time Factors

Substances

  • Hyaluronic Acid
  • Hyaluronoglucosaminidase