title: Novel proteoglycan glycotechnology: chemoenzymatic synthesis of chondroitin sulfate-containing molecules and its application.
abstract: Proteoglycans consist of a protein core, with one or more glycosaminoglycan chains (i.e., chondroitin sulfate, dermatan sulfate and heparin sulfate) bound covalently to it. The glycosaminoglycan chains account for many of the functions and properties of proteoglycans. The development of proteoglycan glycotechnology to exploit the functionality of glycosaminoglycan chains is an extremely important aspect of glycobiology. Here we describe an efficient and widely applicable method for chemoenzymatic synthesis of conjugate compounds comprising intact long chondroitin sulfate (ChS) chains. An alkyne containing ChS was prepared by an enzymatic transfer reaction and linked with a chemically synthesized core compound containing an azido group using click chemistry. This method enabled highly efficient introduction of ChS into target materials. Furthermore, the ChS-introduced compounds had marked stability against proteolysis, and the chemically linked ChS chain contributed to the stability of these core compounds. We believe the present method will contribute to the development of proteoglycan glycobiology and technology.
authors: Department of Organic Chemistry, Faculty of Education, Wakayama University, 930, Sakaedani, Wakayama, 640-8510, Japan. masayama@center.wakayama-u.ac.jp
authors: Masanori
authors: M
authors: Yamaguchi
authors: Keiichi
authors: K
authors: Takagaki
authors: Kaoru
authors: K
authors: Kojima
authors: Naohiro
authors: N
authors: Hayashi
authors: Fengchao
authors: F
authors: Chen
authors: Ikuko
authors: I
authors: Kakizaki
authors: Atsushi
authors: A
authors: Kon
authors: Masahiko
authors: M
authors: Endo
mesh_terms: D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002809:Chondroitin Sulfates / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes; D054794:Glycomics / Q000379:methods*; D007700:Kinetics; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis; D011509:Proteoglycans / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization; D014357:Trypsin / Q000378:metabolism; D014995:Xylosidases / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D010455:Peptides; D011509:Proteoglycans; D002809:Chondroitin Sulfates; D014995:Xylosidases; C026579:exo-1,4-beta-D-xylosidase; D014357:Trypsin