title: Enzymatic polymerization to an alternating N-L-cysteinyl chitin derivative: a novel class of multivalent glycopeptidomimetics.
abstract: A novel chitin derivative with an alternating N-L-cysteinyl group was successfully prepared. The precursor chitin derivative with an alternating N-L-thioprolinyl group could be obtained via chitinase-catalyzed polymerization of the N'-L-thioprolinyl chitobiose oxazoline derivative as a transition state analog substrate monomer under weak alkaline conditions. Conversion of the L-thioprolinyl group to an L-cysteinyl group in the product chitin derivative proceeded in a dose-dependent manner by methoxyamine hydrochloride, and the reaction could be completed almost quantitatively. The obtained chitin derivative is a uniformly amino acid-branching polysaccharide, which is categorized into a novel class of multivalent glycopeptidomimetics.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan. ohmae@peptide.polym.kyoto-u.ac.jp
authors.forename: Masashi
authors.initials: M
authors.lastname: Ohmae
authors.forename: Sanae
authors.initials: S
authors.lastname: Koide
authors.forename: Yuki
authors.initials: Y
authors.lastname: Fujita
authors.forename: Shunsaku
authors.initials: S
authors.lastname: Kimura
mesh_terms: D019843:Archaeal Proteins / Q000737:chemistry*; D002384:Catalysis; D002686:Chitin / Q000031:analogs & derivatives / Q000737:chemistry*; D002688:Chitinases / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D057786:Peptidomimetics / Q000737:chemistry*; D058105:Polymerization; D020027:Pyrococcus furiosus / Q000737:chemistry; D013439:Sulfhydryl Reagents / Q000737:chemistry
chemical_list: D019843:Archaeal Proteins; D004187:Disaccharides; D006020:Glycopeptides; D010080:Oxazoles; D057786:Peptidomimetics; D013439:Sulfhydryl Reagents; D002686:Chitin; C032438:chitobiose; D002688:Chitinases; D003545:Cysteine
keywords: Amino acids; Chitin; Chitinase; Enzyme catalysis; Oxazoline; Polymerization