Glycosides having chromophores as substrates for sensitive enzyme analysis. V. Synthesis of 6'-O-substituted 2',7'-dichlorofluorescein N- acetyl-β-D-glucosaminides as substrates for the rate-assay of N-acetyl-β- D-glucosaminidase

Article abstract of DOI:10.1248/cpb.41.1513

Sixteen novel 6'-O-substituted 2',7'-dichlorofluorescein N-acetyl-β-D- glucosaminides (2a-p) were synthesized from 2',7'-dichlorofluorescein 2,3,4,6-tetraacetyl-β-D-glucosaminide (10), prepared through 3 steps from 2',7'-dichlorofluorescein (3). These N-acetyl-β-D-glucosaminides were examined to evaluate their solubility under the weakly acidic rate-assay conditions (pH 5.0) and their kinetic parameters with N-acetyl-β-D- glucosaminidase. Among these compounds, 6'-O-carboxymethyl- (2a), 6'-O-(N,N- dimethylaminoethyl)- (2i), and 6'-O-sulfoxyethyl-2',7'-dichlorofluorescein N- acetyl-β-D-glucosaminides (2p), are considered to be potential chromogenic substrates for the rate-assay of N-acetyl-β-D-glucosaminidase, since they showed good solubility of more than 10 mM, moderate K(m) values of 1.46-2.04 mM, and higher sensitivity to the enzyme than 2-chloro-4-nitrophenyl-N- acetyl-β-D-glucosaminide.

Full text of DOI:10.1248/cpb.41.1513

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