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Thioglycosides

Thioglycosides are a class of organic compounds characterized by the presence of a thioglycosidic bond, which is a glycosidic bond where the oxygen atom is replaced by a sulfur atom. This structural modification can significantly alter the properties of the molecule compared to its oxygen-containing counterpart. Thioglycosides are often used in chemical synthesis and biological research due to their unique reactivity and stability.

The synthesis of thioglycosides typically involves the reaction of a thiol with a glycosyl donor, such as

In biological contexts, thioglycosides have been studied for their potential as inhibitors of glycosidases, enzymes that

Thioglycosides have also been explored for their potential as glycosidase mimics, which can be used to study

a
glycosyl
halide
or
a
glycosyl
triflate.
The
reaction
proceeds
through
the
formation
of
a
glycosyl-thiolate
intermediate,
which
then
undergoes
nucleophilic
substitution
to
yield
the
thioglycoside.
The
use
of
thioglycosides
in
glycosylation
reactions
has
gained
attention
in
recent
years
due
to
their
ability
to
form
stable
and
selective
glycosidic
bonds
under
mild
conditions.
catalyze
the
hydrolysis
of
glycosidic
bonds.
The
sulfur
atom
in
the
thioglycosidic
bond
can
mimic
the
transition
state
of
the
glycosidase-catalyzed
reaction,
leading
to
potent
and
selective
inhibition.
This
property
has
made
thioglycosides
valuable
tools
in
the
development
of
therapeutic
agents
for
various
diseases,
including
cancer
and
infectious
diseases.
the
mechanism
of
glycosidase-catalyzed
reactions
and
to
design
new
glycosidase
inhibitors.
The
unique
properties
of
thioglycosides
make
them
a
versatile
class
of
compounds
with
wide-ranging
applications
in
chemistry
and
biology.