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Article

Hyaluronidase-Catalyzed Copolymerization for the Single-Step Synthesis of Functionalized Hyaluronan Derivatives

Hirofumi Ochiai, Masashi Ohmae, Tomonori Mori,^† and Shiro Kobayashi*^‡

Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

Biomacromolecules, 2007, 8 (4), pp 1327–1332

DOI: 10.1021/bm061136d

Publication Date (Web): March 23, 2007

†

Present address: RIKEN, The Institute of Physical and Chemical Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. Tel: +81-48-467-9431. E-mail: t-mori@riken.jp.

Corresponding author. Tel/Fax: +81-75-724-7688. E-mail: kobayash@kit.ac.jp.

‡

Present address: R&D Center for Bio-based Materials, Kyoto Institute of Technology, Kyoto 606-8585, Japan.

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 [GlcAβ(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.