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iminosugar

Iminosugars are a class of sugar analogs in which the ring oxygen of the typical sugar ring (pyranose or furanose) is replaced by a nitrogen atom, producing nitrogen-containing cyclic compounds that resemble monosaccharides. They can be natural products found in some plants and microorganisms or synthetic derivatives designed to mimic the shape of sugars. The core structures are usually five- or six-membered rings, such as pyrrolidine- or piperidine-based systems, and the molecules are generally chiral.

Mechanistically, iminosugars most often act as glycosidase inhibitors. By adopting conformations that resemble the transition state

Clinically, several iminosugars have been developed as drugs. Miglitol and voglibose are oral alpha-glucosidase inhibitors used

Safety considerations include gastrointestinal side effects due to undigested carbohydrates, and systemic exposure varies with each

of
glycosidic
bond
cleavage,
they
bind
to
carbohydrate-processing
enzymes
and
block
the
hydrolysis
of
glycosidic
bonds
in
polysaccharides
and
glycoproteins.
This
inhibition
can
reduce
carbohydrate
digestion
in
the
gut
or
alter
intracellular
processing
of
glycoconjugates,
depending
on
the
compound
and
its
pharmacokinetic
properties.
Because
of
this
mode
of
action,
iminosugars
are
used
as
research
tools
and
as
leads
for
therapies
targeting
diseases
related
to
carbohydrate
metabolism
and
glycoprotein
processing.
to
slow
carbohydrate
digestion
in
type
2
diabetes.
Miglustat
(N-butyl-deoxynojirimycin)
is
approved
for
certain
lysosomal
storage
disorders
and
is
used
as
a
substrate-reduction
therapy.
Beyond
medicine,
iminosugars
continue
to
be
explored
for
antiviral
research
and
for
studies
of
glycoprotein
folding
and
trafficking.
compound.