Synthesis of 4-methylumbelliferyl-rutinoside: a new fluorogenic substrate to seek for diglycosidases,

L. S MAZZAFERRO; L. PINUEL; S.L. GIUDICESSI; J.D. BRECCIA; ERRA BALSELLS, ROSA

CARBOHYDRATE RESEARCH

ELSEVIER SCI LTD

Lugar: Amsterdam; Año: 2012 vol. 347 p. 69 - 75

0008-6215

Summary  The enzymatic synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside was performed by the fungal enzyme á-rhamnosyl-â-glucosidase in one transglycosylation step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. The compound was produced in an agitated reactor using the inmovilized catalyst with a 16% yield. 4-Methylumbelliferyl-rutinoside was purified and MALDI-TOF/TOF data recorded for the [M+Na]+ ions indicate that the observed mass correlates with the theoretical monoisotopic mass (calc. [M+Na]+: 507.44 m/z; obs. [M+Na]+:  507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the posibility to explore in nature the ocurrence of endo-â-glucosidases (“diglycosidases”) by zymographic analysis.