Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(36)
Опубликована: Июнь 5, 2024
Previous
N-glycosylation
approaches
have
predominately
involved
acidic
conditions,
facing
challenges
of
low
stereoselectivity
and
limited
scope.
Herein,
we
introduce
a
radical
activation
strategy
that
enables
versatile
stereoselective
using
readily
accessible
glycosyl
sulfinate
donors
under
basic
conditions
exhibits
exceptional
tolerance
towards
various
N-aglycones
containing
alkyl,
aryl,
heteroaryl
nucleobase
functionalities.
Preliminary
mechanistic
studies
indicate
pivotal
role
iodide,
which
orchestrates
the
formation
from
subsequent
generation
key
intermediate,
configurationally
well-defined
is
subsequently
attacked
by
an
N-aglycone
in
stereospecific
S
Molecules,
Год журнала:
2025,
Номер
30(9), С. 2053 - 2053
Опубликована: Май 5, 2025
Given
the
crucial
roles
of
carbohydrates
in
energy
supply,
biochemical
processes,
signaling
events
and
pathogenesis
several
diseases,
development
carbohydrate
analogues,
called
glycomimetics,
is
a
key
research
area
Glycobiology,
Pharmacology,
Medicinal
Chemistry.
Among
many
structural
transformations
explored,
replacement
endo-
exocyclic
oxygen
atoms
by
carbon
(carbasugars)
or
heteroatoms,
such
as
nitrogen
(aza-
iminosugars),
phosphorous
(phosphasugars),
sulfur
(thiosugars),
selenium
(selenosugars)
tellurium
(tellurosugars)
have
garnered
significant
attention.
These
isosteric
substitutions
can
modulate
bioavailability,
stability,
bioactivity,
while
introducing
new
properties,
redox
activity,
interactions
with
pathological
lectins
enzymes,
cytotoxic
effects.
In
this
manuscript
we
focused
on
three
major
families
glycomimetics:
thio-,
seleno-,
tellurosugars.
We
provide
comprehensive
review
most
relevant
synthetic
pathways
leading
to
primarily
at
endocyclic
glycosidic
positions.
The
scope
includes
metal-catalyzed
reactions,
organocatalysis,
electro-
photochemical
transformations,
free-radical
automated
syntheses.
Additionally,
mechanistic
insights,
stereoselectivity,
biological
properties
are
also
discussed.
diversity
promising
bioactivities
these
glycomimetics
underscore
their
significance
area.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(36)
Опубликована: Июнь 5, 2024
Previous
N-glycosylation
approaches
have
predominately
involved
acidic
conditions,
facing
challenges
of
low
stereoselectivity
and
limited
scope.
Herein,
we
introduce
a
radical
activation
strategy
that
enables
versatile
stereoselective
using
readily
accessible
glycosyl
sulfinate
donors
under
basic
conditions
exhibits
exceptional
tolerance
towards
various
N-aglycones
containing
alkyl,
aryl,
heteroaryl
nucleobase
functionalities.
Preliminary
mechanistic
studies
indicate
pivotal
role
iodide,
which
orchestrates
the
formation
from
subsequent
generation
key
intermediate,
configurationally
well-defined
is
subsequently
attacked
by
an
N-aglycone
in
stereospecific
S
