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Enzymatic polymerization to artificial hyaluronic acid using a transition state analogue monomer
Author(s) -
Kobayashi Shiro,
Morii Hidekazu,
Ito Ryosuke,
Ohmae Masashi
Publication year - 2002
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/1521-3900(200207)183:1<127::aid-masy127>3.0.co;2-r
Subject(s) - hyaluronic acid , monomer , polymerization , chemistry , oxazoline , hyaluronidase , polymer chemistry , catalysis , enzyme , combinatorial chemistry , organic chemistry , biochemistry , polymer , biology , genetics
Artificial hyaluronic acid has been synthesized in vitro via enzymatic polymerization catalyzed by testicular hyaluronidases, which is the first successful example of the hyaluronic acid synthesis via non‐biosynthetic pathways. The novel GlcA β (1→3)GlcNAc oxazoline derivative was designed and synthesized as a transition state analogue monomer for the hyaluronidase catalysis. The oxazoline monomer was efficiently recognized by the enzymes at pH 7.1 to 9.0 and the polymerization reaction proceeded in a regio‐ and stereo‐selective manner to give rise to artificial hyaluronic acid with molecular weight higher than 15000. These results strongly suggest that the transition state of these testicular hyaluronidases catalysis corresponds to a sugar oxazolinium ion.