1 research outputs found
Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of α‑d‑Glucosides Using Sucrose Phosphorylase
Thanks
to its broad acceptor specificity, sucrose phosphorylase (SP) has
been exploited for the transfer of glucose to a wide variety of acceptor
molecules. Unfortunately, the low affinity (<i>K</i><sub>m</sub> > 1 M) of SP towards these acceptors typically urges the
addition of cosolvents, which often either fail to dissolve sufficient
substrate or progressively give rise to enzyme inhibition and denaturation.
In this work, a buffer/ethyl acetate ratio of 5:3 was identified to
be the optimal solvent system, allowing the use of SP in biphasic
systems. Careful optimization of the reaction conditions enabled the
synthesis of a range of α-d-glucosides, such as cinnamyl
α-d-glucopyranoside, geranyl α-d-glucopyranoside,
2-<i>O</i>-α-d-glucopyranosyl pyrogallol,
and series of alkyl gallyl 4-<i>O</i>-α-d-glucopyranosides. The usefulness of biphasic catalysis was further
illustrated by comparing the glucosylation of pyrogallol in a cosolvent
and biphasic reaction system. The acceptor yield for the former reached
only 17.4%, whereas roughly 60% of the initial pyrogallol was converted
when using biphasic catalysis