Tryptophan-specific modification and diversification of peptides and proteins
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
This
review
provides
an
account
of
the
tryptophan-specific
conjugation
peptides
and
proteins
its
extensive
application
in
imaging
living
cells,
radiolabelling
proteins,
protein
engineering,
etc
.
Язык: Английский
Halogenase-Assisted Alkyne/Aryl Bromide Sonogashira Coupling for Ribosomally Synthesized Peptides
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(44), С. 30009 - 30013
Опубликована: Окт. 23, 2024
We
describe
the
enzymatic
bromination
of
ribosomally
synthesized
peptides
and
develop
protocols
for
Sonogashira
coupling
peptidic
aryl
bromides
with
a
panel
alkynes.
Using
this
workflow,
entirely
new
chemical
handles
are
introduced
onto
ribosomal
peptides,
including
but
not
limited
to
terminal
alkynes,
which
enable
further
diversification
via
alkyne–azide
click
chemistry.
Regiospecific
installation
bromide
circumvents
genetic
code
expansion
passivation
other
reactive
on
peptide
chain,
representing
applicability
biocatalysts
in
modification
Язык: Английский
Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates: Toward Bisconjugation and Macrocyclization
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 14, 2025
A
facile,
mild,
and
scalable
late-stage
N-alkenylative
modification
strategy
is
introduced
on
1H-indoles,
9H-carbazoles,
their
structural
derivatives
analogues,
including
alkaloids,
bioactive
agents,
tryptophan
motifs,
via
chemo-
regioselective
phosphine-mediated
propiolate
hydroamination.
Saliently,
through
this
protocol,
bisconjugation
macrocyclization
(bis)indolic
scaffolds
can
also
be
accomplished,
with
the
installation
of
new
α,β-unsaturated
ester
handles
for
potential
further
versatile
synthetic
manipulations.
Язык: Английский
Beyond Peptides and Peptidomimetics: Natural Heteroaromatic Amino Acids in the Synthesis of Fused Heterocyclic Frameworks for Bioactive Agents
Organics,
Год журнала:
2025,
Номер
6(2), С. 23 - 23
Опубликована: Май 21, 2025
Heterocycle
cores
are
widely
used
in
medicinal
chemistry
for
developing
bioactive
compounds.
In
this
scenario,
using
cheap
and
accessible
starting
material
to
build
these
heterocycles
is
desirable
obtain
new
drug
candidates
cost-efficient
processes.
One
easily
source
of
amino
acids.
Usually,
compounds
employed
peptide
synthesis,
but
their
use
building
heterocycle
frameworks
presents
another
appealing
opportunity.
Therefore,
review
highlights
the
application
histidine
tryptophan,
two
heteroaromatic
acids,
fused
heterocyclic
scaffold
synthesis
Язык: Английский
Mild Lewis-Acid-Promoted Cysteine–Tryptophan Conjugation Involving a Radical Process
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 4, 2025
Numerous
methods
have
been
developed
for
peptide
synthesis
due
to
their
great
potential
in
drug
discovery.
However,
the
technique
tryptophan-cysteine
conjugation
is
still
underexplored.
Herein,
we
present
a
TMSBr-promoted
ligation
of
tryptophan
and
cysteine
under
mild
conditions
by
using
sulfonate-modified
substrate.
This
protocol
features
broad
scope
high
site
selectivity
applicable
cyclic
peptide.
Preliminary
mechanistic
studies
reveal
that
reaction
proceeds
via
radical
process.
Язык: Английский