Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(30)
Published: May 24, 2023
Abstract
We
present
the
synthesis
of
1,1‐bis(fluorosulfonyl)‐2‐(pyridin‐1‐ium‐1‐yl)ethan‐1‐ide,
a
bench‐stable
precursor
to
ethene‐1,1‐disulfonyl
difluoride
(EDSF).
The
novel
SuFEx
reagent,
EDSF,
is
demonstrated
in
preparation
26
unique
1,1‐bissulfonylfluoride
substituted
cyclobutenes
via
cycloaddition
reaction.
regioselective
click
reaction
rapid,
straightforward,
and
highly
efficient,
enabling
generation
functionalized
4‐membered
ring
(4MR)
carbocycles.
These
carbocycles
are
valuable
structural
motifs
found
numerous
bioactive
natural
products
pharmaceutically
relevant
small
molecules.
Additionally,
we
showcase
diversification
cyclobutene
cores
through
selective
Cs
2
CO
3
‐activated
chemistry
between
single
S−F
group
an
aryl
alcohol,
yielding
corresponding
sulfonate
ester
with
high
efficiency.
Finally,
density
functional
theory
calculations
offer
mechanistic
insights
about
pathway.
National Science Review,
Journal Year:
2023,
Volume and Issue:
10(6)
Published: April 29, 2023
Abstract
Sulfur
fluoride
exchange
(SuFEx),
a
new
generation
of
click
chemistry,
was
first
presented
by
Sharpless,
Dong
and
co-workers
in
2014.
Owing
to
the
high
stability
yet
efficient
reactivity
SVI–F
bond,
SuFEx
has
found
widespread
applications
organic
synthesis,
materials
science,
chemical
biology
drug
discovery.
A
diverse
collection
linkers
emerged,
involving
gaseous
SO2F2
SOF4
hubs;
SOF4-derived
iminosulfur
oxydifluorides;
O-,
N-
C-attached
sulfonyl
fluorides
sulfonimidoyl
fluorides;
novel
sulfondiimidoyl
fluorides.
This
review
summarizes
progress
these
connectors,
with
an
emphasis
on
analysing
advantages
disadvantages
synthetic
strategies
connectors
based
concept,
it
is
expected
be
beneficial
researchers
rapidly
correctly
understand
this
field,
thus
inspiring
further
development
chemistry.
Journal of Medicinal Chemistry,
Journal Year:
2024,
Volume and Issue:
67(10), P. 7668 - 7758
Published: May 7, 2024
Covalent
inhibitors
and
other
types
of
covalent
modalities
have
seen
a
revival
in
the
past
two
decades,
with
variety
new
targeted
drugs
having
been
approved
recent
years.
A
key
feature
such
molecules
is
an
intrinsically
reactive
group,
typically
weak
electrophile,
which
enables
irreversible
or
reversible
formation
bond
specific
amino
acid
target
protein.
This
often
called
"warhead",
critical
determinant
ligand's
activity,
selectivity,
general
biological
properties.
In
2019,
we
summarized
emerging
re-emerging
warhead
chemistries
to
cysteine
acids
(Gehringer,
M.;
Laufer,
S.
A.
J.
Med.
Chem.
62,
5673−5724;
DOI:
10.1021/acs.jmedchem.8b01153).
Since
then,
field
has
rapidly
evolved.
Here
discuss
progress
on
warheads
made
since
our
last
Perspective
their
application
medicinal
chemistry
chemical
biology.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(33)
Published: March 24, 2023
Sulfur(VI)-fluoride
exchange
linkage
as
a
next
generation
of
click
chemistry
was
introduced
by
Sharpless
and
coworkers
in
2014.
Distinguished
from
CuAAC,
the
SuFEx
reaction
proceeds
under
metal-free
conditions,
reactive
linkers
are
variable,
enabling
access
to
diverse
class
compounds.
Therein,
series
emerged
has
been
widely
prevalent
fields.
The
SVI
-F
bond
comparison
-Cl
features
excellent
stability
chemoselectivity.
primarily
involves
formation
S-O
S-N
bonds
via
commercially
available
phenols
amines,
yet
less
study
on
C-SuFEx
linkage.
This
review
will
focus
three
types
for
comprising
S-O,
S-N,
S-C
bonds,
we
hope
provide
practical
guidance
chemistry.
Aggregate,
Journal Year:
2023,
Volume and Issue:
4(4)
Published: March 26, 2023
Abstract
The
development
of
rapid,
selective,
and
sensitive
fluorescent
sensors
is
essential
for
visualizing
quantifying
biological
molecules
processes
in
vitro,
ex
vivo,
which
important
not
only
fundamental
studies
but
the
accurate
diagnosis
diseases.
emerging
field
activity‐based
sensing
(ABS),
a
method
that
utilizes
molecular
reactivity
analyte
detection
possesses
many
advantages
including
high
specificity,
sensitivity
accuracy.
aggregation
caused
quenching
phenomenon
occurs
most
conventional
fluorophores
results
reduced
labeling
efficiency
target
analytes
low
photobleaching
resistance,
therefore
limiting
applications
ABS
strategy.
In
contrast,
induced
emission
(AIE)
active
luminogens
(AIEgens)
provide
exceptional
frameworks
ABS.
Of
reaction
classes
utilized
AIEgen
approach,
click
chemistry
has
become
increasing
popular.
this
review,
concepts
approach
with
AIEgens
principles
are
discussed,
followed
by
systematic
summary
application
specific
reactions
protocols
an
array
analytes.
Furthermore,
utility
construction
bioimaging
will
also
be
showcased
throughout
review.
Chem,
Journal Year:
2024,
Volume and Issue:
10(6), P. 1868 - 1884
Published: March 5, 2024
Phosphorus
fluoride
exchange
(PFEx),
recently
debuted
in
small
molecules,
represents
the
forefront
of
click
chemistry.
To
explore
PFEx's
potential
biological
settings,
we
developed
amino
acids
phosphoramidofluoridate
tyrosine
(PFY)
and
lysine
(PFK)
featuring
phosphoramidofluoridates
incorporated
them
into
proteins
through
genetic
code
expansion.
PFY/PFK
selectively
reacted
with
nearby
His,
Tyr,
Lys,
or
Cys
proteins,
both
vitro
living
cells,
demonstrating
that
proximity
enabled
PFEx
reactivity
without
external
reagents.
The
reaction
His
showed
unique
pH-dependent
properties
created
thermally
sensitive
linkages.
Additionally,
Na2SiO3
enhanced
reactions
Tyr
Cys.
PFEx,
by
generating
defined
covalent
P-N/O
linkages,
extends
utility
phosphorus
linkages
aligning
nature's
use
phosphate
connectors
other
biomolecules.
More
versatile
durable
than
sulfur
(SuFEx),
expands
latent
bioreactive
arsenal
for
protein
engineering
will
facilitate
broad
application
this
potent
chemistry
biomedical
fields.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(11), P. 3879 - 3892
Published: Jan. 1, 2024
The
Accelerated
SuFEx
Click
Chemistry
(ASCC)
protocol,
adapted
to
a
96-well
plate
format,
has
been
applied
the
late-stage
derivatization
of
bioactive
molecules
and
array
synthesis
anticancer
agents,
showcasing
its
potential
for
drug
discovery.
