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Synthesis of chromogenic probes for detection and assay of diglycosidases


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Synthesis of chromogenic probes for detection and assay of diglycosidases

Matej Cvečko 1 Peter Kis 1 Mária Mastihubová 1 Vladimír Mastihuba 1

1Chemický ústav SAV, Bratislava, Slovenská republika
matej.cvecko@gmail.com

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.[1] Four yet known diglycosidases, namely rutinosidase/hesperidinase, acuminosidase, vicianosidase, and primeverosidase may be considered as endo-β-glucosidases, [2] since they hydrolyze β-glycosidic bond between aglycone and glucose, with another saccharide moiety (e.g. rhamnopyranosyl, apiofuranosyl, xylopyranosyl, arabinopyranosyl) [3] 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.

This work was supported by the Slovak Research and Development Agency under the contract No. APVV-18-0188 and by the Slovak Grant Agency for Science VEGA (grant number 2/0126/19). The work was inspired by scientific interactions that evoved within the COST Action CA18103 - Innovation with Glycans: new frontiers from synthesis to new biological targets (INNOGLY).
[1] Sakata, K.; Mizutani, M.; Ma, S. J.; Hiratake, J. Methods Enzymol., 2003, 363, 444-459.
[2] Mazzaferro, L. S.; Breccia, J. D. Biocatal. Biotrans. 2011, 29, 103-112.
[3] Koseki, T.; Ishikawa, M.; Kawasaki, M.; Shiono, Y. Appl. Microbiol. Biotechnol. 2018, 102, 8717-8723.
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Diskusia

? diglykozidazy 18.05.2021 09:01
Dobry den, pekny praca, blahozelam k vysledkom. Mohli by ste, prosim Vas, pre "laikov" a ostatnych ucastnikov konfrencie PREVEDA 2021 objasnit vyuzitie a aplikacny potencial glykozidaz, aby sme si ...Zobraziť celý komentár
Matej Cvečko
Pasívny
Re: ? diglykozidazy 19.05.2021 18:57
Dobrý deň, ďakujem za Vašu otázku aj za kladné ohodnotenie. Glykozidázy nekatalyzujú iba štiepenie glykozidovej väzby, ale aj jej vznik. To znamená, že môžu byť použité ako nástroj pre synt...Zobraziť celý komentár
Re: Re: ? diglykozidazy 20.05.2021 05:18
Dakujem za doplnenie, vela stastia a uspechov do vasej dalsej prace. S pozdravom, ZB
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