Synthesis of chromogenic probes for detection and assay of diglycosidases
Matej Cvečko 1
Peter Kis 1
Mária Mastihubová 1
Vladimír Mastihuba 1
1 Chemický ústav SAV, Bratislava, Slovenská republika
|Section:||Organic, bioorganic and pharmaceutical chemistry, pharmacology and toxicology|
Diglycosidases represent a special group of glycoside hydrolases characterized by their unique way of hydrolysis of natural products, such as rutin, hesperidin, furcatin, vicianin, etc. Four yet known diglycosidases, namely rutinosidase/hesperidinase, acuminosidase, vicianosidase, and primeverosidase may be considered as endo-β-glucosidases,  since they hydrolyze β-glycosidic bond between aglycone and glucose, with another saccharide moiety (e.g. rhamnopyranosyl, apiofuranosyl, xylopyranosyl, arabinopyranosyl)  bound in the position 6-O of the glucopyranoside ring.
In this work we synthesized two derivatives of natural disaccharides 4-nitrophenyl β-acuminoside (1) and 2-nitrophenyl β-robinobioside (2) as chromogenic probes of two diglycosidases – acuminosidase and robinobiosidase, respectively. The key steps of synthesis were glycosylations of appropriate peracetylated nitrophenyl glycosides previously deprotected in position 6, with peracetylated D-apiofuranosyl donor or D-rhamnopyranosyl donor, respectively. Two different glycosylation methods were used, resulting in good yields and excellent stereoselectivity. After deprotection of glycosylation products we obtained 43 % of 1 and 83% of 2 overall in two steps. We intend to use these compounds as chromogenic probes for two diglycosidases – acuminosidase and robinobiosidase.
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