Organic Letters,
Год журнала:
2024,
Номер
26(24), С. 5130 - 5135
Опубликована: Июнь 6, 2024
An
efficient
and
concise
strategy
for
the
synthesis
of
cyclic
dipeptides
via
Pd-catalyzed
site-selective
δ-C(sp2)–H
amination/fluorination
N-to-C
cyclization
is
disclosed.
The
backbone
amides
within
serves
as
endogenous
directing
groups,
while
desired
products
were
switched
by
C-terminal
ester
group.
This
chemistry
presents
a
novel
robust
alternative
to
construct
cyclodipeptide
fragments.
RSC Medicinal Chemistry,
Год журнала:
2021,
Номер
12(8), С. 1325 - 1351
Опубликована: Янв. 1, 2021
Macrocyclization
between
head,
tail
or
sidechains
is
a
frequently
employed
strategy
to
enhance
peptide
and
peptidomimetic
stability,
selectivity
affinity.
Chemical Society Reviews,
Год журнала:
2021,
Номер
50(16), С. 9278 - 9343
Опубликована: Янв. 1, 2021
Peptide
modifications
can
unlock
a
variety
of
compounds
with
structural
diversity
and
abundant
biological
activity.
In
nature,
peptide
modifications,
such
as
functionalisation
at
the
side-chain
position
amino
acids,
are
performed
using
post-translational
modification
enzymes
or
incorporation
unnatural
acids.
However,
accessing
these
remains
challenge
for
organic
chemists.
During
past
decades,
selective
C-H
activation/functionalisation
has
attracted
considerable
attention
in
synthetic
chemistry
pathway
to
modification.
Various
directing
group
strategies
have
been
discovered
that
assist
activation.
particular,
bidentate
groups
enable
tuneable
reversible
coordination
now
recognised
one
most
efficient
methods
site-selective
activation
numerous
families
compounds.
Synthetic
chemists
harnessed
β-
γ-positions
This
method
expanded
an
effective
device
late
stage
macrocyclisation
total
synthesis
complex
natural
products.
this
review,
we
discuss
various
β-,
γ-,
δ-C(sp3)-H
bond
reactions
acids
formation
C-X
bonds
aid
their
application
late-stage
Pharmacological Research,
Год журнала:
2024,
Номер
203, С. 107137 - 107137
Опубликована: Март 23, 2024
Peptide
stapling,
by
employing
a
stable,
preformed
alpha-helical
conformation,
results
in
the
production
of
peptides
with
improved
membrane
permeability
and
enhanced
proteolytic
stability,
compared
to
original
peptides,
provides
an
effective
solution
accelerate
rapid
development
peptide
drugs.
Various
reviews
present
stapling
chemistries,
anchoring
residues
one-
or
two-component
cyclization,
however,
therapeutic
stapled
have
not
been
systematically
summarized,
especially
focusing
on
various
disease-related
targets.
This
review
highlights
latest
advances
drug
facilitated
application
technology,
including
different
techniques,
synthetic
accessibility,
applicability
biological
targets,
potential
for
solving
problems,
as
well
current
status
development.
Stapled
candidates
classified
analysed
mainly
receptor-
ligand-based
design
against
diseases,
cancer,
infectious
inflammation,
diabetes.
is
expected
provide
comprehensive
reference
rational
diseases
targets
facilitate
pharmacokinetic
properties.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(23), С. 6720 - 6759
Опубликована: Янв. 1, 2021
Exciting
developments
in
the
site-selective
modification
of
peptide
backbones
are
allowing
an
outstanding
fine-tuning
conformation,
folding
ability,
and
physico-chemical
biological
properties.
Chemical Communications,
Год журнала:
2022,
Номер
58(16), С. 2612 - 2633
Опубликована: Янв. 1, 2022
Advancements
in
the
palladium-catalyzed
functionalization
of
diastereotopic
or
prochiral
C(sp
3
)–H
bonds
generating
stereogenic
centers
and
stereo-arrays
aliphatic
compounds
have
been
highlighted.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(31)
Опубликована: Май 23, 2022
Transition
metal-catalyzed
C-H
activation
is
a
step-economical
strategy
for
peptide
functionalization.
Herein,
we
report
the
method
of
late-stage
ligation
and
macrocyclization
through
rhodium-catalyzed
alkylation
tryptophan
residues
at
C7
position.
This
utilizes
N-Pt
Bu2
directing
group
tolerates
various
alkene
substrates.
Utilizing
internal
olefins,
this
study
represents
first
example
site-selective
deconjugative
isomerization.
Furthermore,
our
provides
access
to
macrocycles
with
unique
Trp(C7)-alkyl
crosslinks
potent
cytotoxicity
towards
cancer
cells.
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3991 - 3996
Опубликована: Май 1, 2024
Peptide
modification
by
C(sp3)–H
functionalization
of
residues
at
the
internal
positions
remains
underdeveloped
due
to
inhibitory
effect
backbone
amides.
In
this
study,
using
histidine
(His)
as
an
endogenous
directing
group,
we
developed
a
novel
method
for
β-C(sp3)–H
alanine
(Ala)
diverse
peptides.
Through
approach,
wide
range
linear
peptides
were
modified
on
side-chain
Ala
adjacent
His
afford
functionalized
in
moderate
good
yield
and
excellent
position
selectivity.
Furthermore,
conjugation
with
functional
molecules
such
glucuronide,
oleanolic
acid,
dipeptide,
fluorophore
derivatives
was
achieved.
Chemical Science,
Год журнала:
2021,
Номер
12(23), С. 8073 - 8078
Опубликована: Янв. 1, 2021
Precise
structural
modifications
of
amino
acids
are
importance
to
tune
biological
properties
or
modify
therapeutical
capabilities
relevant
drug
discovery.
