Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
27(1), P. 69 - 88
Published: Sept. 15, 2020
Abstract
Photochemical
reactions
have
been
the
subject
of
renewed
interest
over
last
two
decades,
leading
to
development
many
new,
diverse
and
powerful
chemical
transformations.
More
recently,
these
developments
expanded
enable
photochemical
macrocyclisation
peptides
small
proteins.
These
constructs
benefit
from
increased
stability,
structural
rigidity
biological
potency
their
linear
counterparts,
providing
opportunities
for
improved
therapeutic
agents.
In
this
review,
an
overview
both
established
emerging
methods
peptide
is
presented,
highlighting
limitations
further
innovation
in
field.
RSC Medicinal Chemistry,
Journal Year:
2021,
Volume and Issue:
12(8), P. 1325 - 1351
Published: Jan. 1, 2021
Macrocyclization
between
head,
tail
or
sidechains
is
a
frequently
employed
strategy
to
enhance
peptide
and
peptidomimetic
stability,
selectivity
affinity.
ACS Catalysis,
Journal Year:
2020,
Volume and Issue:
10(18), P. 10551 - 10558
Published: Aug. 17, 2020
Detailed
density
functional
theory
calculations
provide
valuable
insight
into
reactivity-controlling
factors
in
transition
metal-catalyzed
C–H
activation
by
carboxylate
assistance.
The
chelation-assisted
of
a
variety
arenes
3d
and
4d
metal
complexes
was
analyzed
means
bond
order
analysis
through
(DFT)
as
well
energy
decomposition
DLPNO–CCSD(T)
calculations,
thereby
providing
in-depth
information
on
distinct
electronic
influences
the
key
state
demonstrating
preferred
base-assisted
internal
electrophilic
substitution
(BIES)
rather
than
concerted
metalation-deprotonation
(CMD)
pathway.
Chemical Communications,
Journal Year:
2020,
Volume and Issue:
56(90), P. 13950 - 13958
Published: Jan. 1, 2020
Peptides
hold
great
promise
in
proteomics,
diagnostics
and
drug
discovery.
While
natural
peptides
continue
to
be
of
key
importance,
chemically
modified
unnatural
have
been
found
show
enhanced
biological
activities
improved
therapeutic
capabilities
compared
their
counterparts.
Therefore,
the
development
efficient
versatile
strategies
enable
easy
access
is
high
demand.
In
recent
years,
palladium-catalyzed
direct
functionalization
inert
C(sp3)-H
bonds
has
emerged
as
a
powerful
straightforward
synthetic
strategy
for
late-stage
modification
peptides.
this
review,
we
summarize
progress
emerging
field.
For
clarity,
review
organized
into
three
sections
according
peptide
side-chains
at
β-,
γ-,
δ-positions.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(18), P. 3983 - 4001
Published: Jan. 1, 2021
Polypeptide
cyclisation
can
enhance
thermal
stability,
proteolytic
resistance
and
membrane
permeability.
Cyclisation
be
achieved
by
methods
including
chemical,
enzyme
protein
tag
approaches.
Each
has
strengths
limitations.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
12(16), P. 5804 - 5810
Published: Jan. 1, 2021
A
highly
efficient
and
versatile
method
for
construction
of
peptide
macrocycles
via
palladium-catalyzed
intramolecular
S-arylation
alkyl
aryl
thiols
with
iodides
under
mild
conditions
is
developed.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(25), P. 13968 - 13978
Published: June 16, 2023
The
three-dimensional
structure
of
medium-sized
cyclic
peptides
accounts
for
their
biological
activity
and
other
important
physiochemical
properties.
Despite
significant
advances
in
the
past
few
decades,
chemists'
ability
to
fine-tune
structure,
particular,
backbone
conformation,
short
made
canonical
amino
acids
is
still
quite
limited.
Nature
has
shown
that
cross-linking
aromatic
side
chains
linear
peptide
precursors
via
enzyme
catalysis
can
generate
cyclophane-braced
products
with
unusual
structures
diverse
activities.
However,
biosynthetic
path
these
natural
challenging
replicate
synthetic
laboratory
using
practical
chemical
modifications
peptides.
Herein,
we
report
a
broadly
applicable
strategy
remodel
homodetic
by
Trp,
His,
Tyr
residues
various
aryl
linkers.
linkers
be
easily
installed
copper-catalyzed
double
heteroatom-arylation
reactions
diiodides.
These
combined
form
large
variety
assemblies
heteroatom-linked
multi-aryl
units.
serve
as
tension-bearable
multijoint
braces
modulate
conformation
an
entry
previously
inaccessible
conformational
space.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(30), P. 20868 - 20877
Published: July 18, 2024
Contemporary
developments
in
the
field
of
peptide
macrocyclization
methodology
are
imperative
for
enabling
advance
drug
design
medicinal
chemistry.
This
report
discloses
a
Rh(III)-catalyzed
via
carboamidation,
reacting
acryloyl-peptide-dioxazolone
precursors
and
arylboronic
acids
to
form
complex
cyclic
peptides
with
concomitant
incorporation
noncanonical
α-amino
acids.
The
diverse
modular
technology
allows
expedient
access
wide
variety
from
4
15
amino
size
features
simultaneous
formation
unnatural
phenylalanine
tyrosine
derivatives
up
>20:1
diastereoselectivity.
reaction
showcases
an
expansive
substrate
scope
45
examples
is
compatible
majority
standard
protected
used
Fmoc-solid
phase
synthesis.
applied
synthesis
multiple
peptidomimetic
macrocyclic
analogs,
including
cyclosomatostatin
gramicidin
S.
