Beilstein Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
20, P. 3274 - 3280
Published: Dec. 17, 2024
The
rising
popularity
of
bioconjugate
therapeutics
has
led
to
growing
interest
in
late-stage
functionalization
(LSF)
peptide
scaffolds.
α,β-Unsaturated
amino
acids
like
dehydroalanine
(Dha)
derivatives
have
emerged
as
particularly
useful
structures,
the
electron-deficient
olefin
moiety
can
engage
reactions,
a
Giese-type
reaction.
Cheap
and
widely
available
building
blocks
organohalides
be
converted
into
alkyl
radicals
by
means
photoinduced
silane-mediated
halogen-atom
transfer
(XAT)
offer
mild
straightforward
methodology
alkylation.
In
this
research,
we
present
metal-free
strategy
for
photochemical
alkylation
derivatives.
Upon
abstraction
hydride
from
tris(trimethylsilyl)silane
(TTMS)
an
excited
benzophenone
derivative,
formed
silane
radical
undergo
XAT
with
bromide
generate
radical.
Consequently,
undergoes
reaction
Dha
forming
new
C(sp
3
)–C(sp
)
bond.
performed
phosphate-buffered
saline
(PBS)
solution
shows
post-functionalization
prospects
through
pathways
involving
classical
chemistry.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
13(11)
Published: Aug. 16, 2024
Abstract
A
new
approach
of
dual
visible
light‐induced
gold(III)‐catalyzed
alkynylation
and
its
application
in
selective
modification
alkyne‐linked
peptides
has
been
developed.
The
bis‐cyclometalated
gold(III)
complex
exhibited
roles
(1)
situ
generation
quinolizinium‐based
photosensitizer
(λ
em
=500
–
594
nm)
(2)
iminium
ions.
Under
optimized
conditions,
alkynylated
products
were
afforded
good
yields
up
to
73
%.
this
strategy
gave
modified
67
%
conversion.
Our
light/gold(III)
catalysis
exemplifies
the
potential
merging
photocatalysis
transition
metal
develop
novel
bioconjugation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 23, 2024
Chemical
modification
of
proteins
has
been
widely
applied
in
diagnostic
and
therapeutic
processes.
Here,
we
report
a
novel
bioconjugation
between
sulfinic
acids
amino
acid
dehydroalanine
(Dha)
the
context
both
small
molecules
proteins.
This
conjugation
enables
rapid
formation
sulfone
linkages
chemoselective
disulfide-compatible
manner
under
biocompatible
conditions
with
Dha
residues
chemically
installed
thus
provides
robust
tool
that
is
simple
exquisite
site
selectivity
for
protein
functionalization
wide
range.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(36)
Published: June 13, 2024
Abstract
Isotopically
labeled
alkanes
play
a
crucial
role
in
organic
and
pharmaceutical
chemistry.
While
some
deuterated
methylating
agents
are
readily
available,
the
limited
accessibility
of
other
deuteroalkyl
reagents
has
hindered
synthesis
corresponding
products.
In
this
study,
we
introduce
nickel‐catalyzed
system
that
facilitates
various
deuterium‐labeled
through
hydrodeuteroalkylation
d2‐labeled
alkyl
TT
salts
with
unactivated
alkenes.
Diverging
from
traditional
reagents,
thianthrenium
(TT)
can
effectively
selectively
deuterium
at
α
position
chains
using
D
2
O
as
source
via
single‐step
pH‐dependent
hydrogen
isotope
exchange
(HIE).
Our
method
allows
for
high
incorporation,
offers
precise
control
over
site
insertion
within
an
chain.
This
technique
proves
to
be
invaluable
compounds,
especially
those
relevance.
Tetrahedron Chem,
Journal Year:
2024,
Volume and Issue:
11, P. 100088 - 100088
Published: Aug. 1, 2024
While
their
broad
utility
in
various
chemistry
fields
were
well
recognized
for
decades,
fluoroalcohols
have
recently
emerged
as
a
unique
solvent
system
bioconjugation
development.
This
review
describes
examples
and
roles
of
such
trifluoroethanol
(TFE)
hexafluoroisopropanol
(HFIP)
chemical
modification
biomolecules
polypeptides,
nucleic
acids,
saccharides.
Many
processes
facilitated
by
notable
functions
those
proton
shuttle,
reversible
adduct
formation
with
reactive
species,
compatibility
electrochemistry/photochemistry.
The
usefulness
the
fluoroalcohol
solvents
can
be
even
promoted
its
combination
different
reaction
enhancement
protein
stabilization.
collection
transformations
this
is
an
indication
rapid
growth
solvent-assisted
field.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
An
efficient
redox-neutral
palladium-catalyzed
system
has
been
developed
to
introduce
indole
and
pyrrole
various
bioactive
molecules
via
late-stage
aryl
C–H
activation,
providing
a
robust
tool
explore
structure–activity
relationships
(SARs).
Beilstein Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
20, P. 3274 - 3280
Published: Dec. 17, 2024
The
rising
popularity
of
bioconjugate
therapeutics
has
led
to
growing
interest
in
late-stage
functionalization
(LSF)
peptide
scaffolds.
α,β-Unsaturated
amino
acids
like
dehydroalanine
(Dha)
derivatives
have
emerged
as
particularly
useful
structures,
the
electron-deficient
olefin
moiety
can
engage
reactions,
a
Giese-type
reaction.
Cheap
and
widely
available
building
blocks
organohalides
be
converted
into
alkyl
radicals
by
means
photoinduced
silane-mediated
halogen-atom
transfer
(XAT)
offer
mild
straightforward
methodology
alkylation.
In
this
research,
we
present
metal-free
strategy
for
photochemical
alkylation
derivatives.
Upon
abstraction
hydride
from
tris(trimethylsilyl)silane
(TTMS)
an
excited
benzophenone
derivative,
formed
silane
radical
undergo
XAT
with
bromide
generate
radical.
Consequently,
undergoes
reaction
Dha
forming
new
C(sp
3
)–C(sp
)
bond.
performed
phosphate-buffered
saline
(PBS)
solution
shows
post-functionalization
prospects
through
pathways
involving
classical
chemistry.
