The
continuous
development
of
click
reactions
with
new
connecting
linkage
is
crucial
for
advancing
the
frontiers
chemistry.
Selenium-nitrogen
exchange
(SeNEx)
chemistry,
a
versatile
chemistry
in
represents
an
all-encompassing
term
nucleophilic
substitution
events
that
replace
nitrogen
at
electrophilic
selenium(II)
center,
enabling
flexible
and
efficient
assembly
linkages
around
Se(II)
core.
Several
SeNEx
chemistries
have
been
developed
inspired
by
biochemical
reaction
between
Ebselen
cysteine
residue,
demonstrated
significant
potential
on-plate
nanomole-scale
parallel
synthesis,
selenium-containing
DNA-encoded
library
(SeDEL)
as
well
peptide
protein
bioconjugation.
This
concept
aims
to
present
origins,
advancements,
applications
selenium(II)-nitrogen
while
also
outlining
directions
future
research
this
field.
Acta Pharmaceutica Sinica B,
Год журнала:
2023,
Номер
14(2), С. 492 - 516
Опубликована: Окт. 11, 2023
DNA-encoded
chemical
library
(DEL)
links
the
power
of
amplifiable
genetics
and
non-self-replicating
phenotypes,
generating
a
diverse
world.
In
analogy
with
biological
world,
DEL
world
can
evolve
by
using
central
dogma,
wherein
DNA
replicates
PCR
reactions
to
amplify
genetic
codes,
sequencing
transcripts
information,
DNA-compatible
synthesis
translates
into
phenotypes.
Importantly,
is
key
expanding
space.
Besides,
evolution-driven
selection
system
pushes
chemicals
under
selective
pressure,
i.e.,
desired
strategies.
this
perspective,
we
summarized
recent
advances
in
synthetic
toolbox
panning
strategies,
which
will
shed
light
on
drug
discovery
harnessing
vitro
evolution
via
DEL.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(15)
Опубликована: Фев. 12, 2024
Abstract
Click
chemistry
is
a
powerful
molecular
assembly
strategy
for
rapid
functional
discovery.
The
development
of
click
reactions
with
new
connecting
linkage
great
importance
expanding
the
toolbox.
We
report
first
selenium‐nitrogen
exchange
(SeNEx)
reaction
between
benzoselenazolones
and
terminal
alkynes
(Se−N
to
Se−C),
which
inspired
by
biochemical
SeNEx
Ebselen
cysteine
(Cys)
residue
Se−S).
formed
selenoalkyne
connection
readily
elaborated,
thus
endowing
this
multidimensional
diversity.
Besides,
modular,
predictable,
high‐yielding,
features
fast
kinetics
(k2≥14.43
M
−1
s
),
excellent
group
compatibility,
works
well
at
miniaturization
(nanomole‐scale),
opening
up
many
interesting
opportunities
organo‐Se
synthesis
bioconjugation,
as
exemplified
sequential
(coupled
ruthenium‐catalyzed
azide‐alkyne
cycloaddition
(RuAAC)
sulfur‐fluoride
(SuFEx)),
selenomacrocycle
synthesis,
nanomole‐scale
Se‐containing
natural
product
library
DNA‐encoded
(DEL),
late‐stage
peptide
modification
ligation,
multiple
functionalization
proteins.
These
results
indicated
that
useful
developments,
established
will
serve
transformative
platform
in
multidisciplinary
fields
such
synthetic
chemistry,
material
science,
chemical
biology,
medical
drug
Expert Opinion on Drug Discovery,
Год журнала:
2024,
Номер
19(6), С. 725 - 740
Опубликована: Май 16, 2024
Introduction
The
effectiveness
of
Fragment-based
drug
design
(FBDD)
for
targeting
challenging
therapeutic
targets
has
been
hindered
by
two
factors:
the
small
library
size
and
complexity
fragment-to-hit
optimization
process.
DNA-encoded
(DEL)
technology
offers
a
compelling
robust
high-throughput
selection
approach
to
potentially
address
these
limitations.
Chemical Science,
Год журнала:
2022,
Номер
13(44), С. 13100 - 13109
Опубликована: Янв. 1, 2022
Taking
advantage
of
aryl
diazonium
intermediates,
this
work
reported
a
DNA-compatible
C–C
bond
formation
strategy,
achieving
broad
substrate
scope,
exquisite
functional
group
tolerance,
and
orthogonality
to
halide-based
coupling
reactions.
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 7, 2025
Constructing
chemical
bonds
under
green
sustainable
conditions
has
drawn
attention
from
environmental
and
economic
perspectives.
The
dissociation
of
(hetero)aryl-halide
is
a
crucial
step
most
arylations
affording
(hetero)arene
derivatives.
Herein,
we
summarize
the
(hetero)aryl
halides
activation
enabling
direct
(hetero)arylation
trapping
reagents
construction
highly
functionalized
(hetero)arenes
benign
conditions.
strategies
for
aryl
iodides
are
classified
into
(a)
hypervalent
iodoarene
followed
by
functionalization
thermal/photochemical
conditions,
(b)
aryl-I
bond
in
presence
bases
with/without
organic
catalysts
promoters,
(c)
photoinduced
presence/absence
organophotocatalysts,
(d)
electrochemical
direct/indirect
electrolysis
mediated
organocatalysts
mediators
acting
as
electron
shuttles,
(e)
electrophotochemical
redox-active
organocatalysts.
These
modes
result
exhibiting
diverse
reactivity
formal
cations/radicals/anions
aryne
precursors.
coupling
these
reactive
intermediates
with
leads
to
facile
selective
formation
C-C
C-heteroatom
bonds.
ecofriendly,
inexpensive,
functional
group-tolerant
offer
alternatives
transition
metal-based
catalysis.
Abstract
A
successful
DNA‐encoded
library
(DEL)
will
consist
of
diverse
skeletons
and
cover
chemical
space
as
comprehensive
possible
to
fully
realize
its
potential
in
drug
discovery
biology.
However,
the
lack
versatile
on‐DNA
arylation
methods
for
phenols
that
are
less
nucleophilic
reactive
poses
a
great
hurdle
DEL
include
diaryl
ether,
privileged
chemotype
pharmaceuticals
natural
products.
This
work
describes
use
“substrate
activation”
approach
address
DNA‐conjugated
phenols.
Diaryliodonium
salt,
highly
electrophilic
reagent,
is
employed
Ar
+
sources
ensure
selective
oximes
with
both
high
yields
DNA
fidelity.
Notably,
new
reaction
can
be
applied
late‐stage
modification
peptides
containing
tyrosine
side‐chain
synthesize
DNA‐tagged
analogues
existing
molecules
such
sorafenib,
known
pan‐kinase
inhibitor.
The
diaryliodonium
salts
chemistry
affords
greater
flexibility
design
synthesis.
Abstract
An
ideal
DNA‐encoded
library
(DEL)
selection
requires
the
to
consist
of
diverse
core
skeletons
and
cover
chemical
space
as
much
possible.
However,
lack
efficient
on‐DNA
synthetic
approaches
toward
has
greatly
restricted
diversity
DEL.
To
mitigate
this
issue,
work
disclosed
a
“Mask
&
Release”
strategy
streamline
challenging
skeleton
synthesis.
N
‐phenoxyacetamide
is
used
masked
phenol
versatile
directing
group
mediate
diversified
DNA‐compatible
C‐H
functionalization,
introducing
1st‐dimensional
at
defined
site,
simultaneously
releasing
functionality,
which
can
facilitate
introduction
2nd
diversity.
This
not
only
provides
set
syntheses
DNA‐conjugated
drug‐like
such
ortho
‐alkenyl/sulfiliminyl/cyclopropyl
phenol,
benzofuran,
dihydrobenzofuran
but
also
paradigm
for
method
development.
Chemical Communications,
Год журнала:
2024,
Номер
60(59), С. 7638 - 7641
Опубликована: Янв. 1, 2024
DNA-compatible
diversity-oriented
synthesis
of
nitrogen-containing
heterocycles
via
the
in
situ
conversion
primary
amines
into
versatile
isothiocyanates
intermediates.
Chemical Communications,
Год журнала:
2023,
Номер
59(41), С. 6128 - 6147
Опубликована: Янв. 1, 2023
The
hit
finding
strategy
in
drug
discovery
has
undergone
a
tremendous
change
the
past
decade
with
advent
of
DNA-encoded
libraries
diverse
chemical
libraries.
