Chemo- and enzymatic synthesis of partially and fully N-deacetylated 4-methylumbelliferyl chitobiosides: fluorogenic substrates for chitinase.
Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN)2-UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of heterochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources.
Honda
Y
Y
Laboratory of Bioorganic Chemistry, College of Agriculture, Osaka Prefecture University, Sakai, Japan. honda@server.biochem.osakafu-u.ac.jp
Tanimori
S
S
Kirihata
M
M
Kaneko
S
S
Tokuyasu
K
K
Hashimoto
M
M
Watanabe
T
T
D001407:Bacillus / Q000201:enzymology; D002240:Carbohydrate Sequence; D002688:Chitinases / Q000378:metabolism*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000378:metabolism*; D013379:Substrate Specificity
D004187:Disaccharides; D005456:Fluorescent Dyes; D002688:Chitinases