Chitinase-catalyzed synthesis of alternatingly N-deacetylated chitin: a chitin-chitosan hybrid polysaccharide.
A chitin-chitosan hybrid polysaccharide (2) having a beta(1-->4)-linked alternating structure of an N-acetyl-D-glucosamine (GlcNAc) unit and a D-glucosamine (GlcN) unit was synthesized via chitinase-catalyzed polymerization of an oxazoline derivative of a GlcNbeta(1-->4)GlcNAc monomer (1). Monomer 1 was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis, which belongs to the glycoside hydrolase family 18. Monomer 1 was effectively polymerized by the catalysis of enzymes from Bacillus sp., Serratia marcescens and Streptomyces griseus, under weak alkaline conditions, giving rise to a water-soluble hybrid polysaccharide (2) in good yields. Molecular weights of 2 reached 2,020 with using chitinase from Serratia marcescens, which corresponds to 10-12 saccharide units.
Makino
Akira
A
Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
Kurosaki
Kazuhiro
K
Ohmae
Masashi
M
Kobayashi
Shiro
S
D000107:Acetylation; D001407:Bacillus / Q000378:metabolism; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D002686:Chitin / Q000737:chemistry*; D002688:Chitinases / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011108:Polymers / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry; D012706:Serratia marcescens / Q000378:metabolism; D013305:Streptomyces griseus / Q000378:metabolism
D011108:Polymers; D011134:Polysaccharides; D002686:Chitin; D002688:Chitinases