Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(29)
Published: May 10, 2022
Abstract
LPt
IV
F(Aryl)
complexes
bearing
a
bulky
bidentate
2‐[bis(adamant‐1‐yl)phosphino]phenoxide
ligand
(L)
demonstrate
excellent
reactivity
and
selectivity
in
the
arylation
of
X−H
(X=S,
N)
bonds
amino
acid
residues
unprotected
peptides
under
mild,
including
aqueous,
conditions.
Stepwise
addition
these
allowed
convenient
one‐pot
introduction
different
aromatic
groups
Cys
N
terminus.
Pt
reagents
can
also
be
used
to
further
arylate
N−H
Lys
Trp
providing
access
multiple
groups.
Quarterly Reviews of Biophysics,
Journal Year:
2022,
Volume and Issue:
55
Published: Jan. 1, 2022
Abstract
Trp
is
unique
among
the
amino
acids
since
it
involved
in
many
different
types
of
noncovalent
interactions
such
as
electrostatic
and
hydrophobic
ones,
but
also
π-π,
π-cation,
π-anion
π-ion
pair
interactions.
In
membranotropic
peptides
proteins,
locates
preferentially
at
water-membrane
interface.
antimicrobial
or
cell-penetrating
(AMPs
CPPs
respectively),
well-known
for
its
strong
role
capacity
these
to
interact
affect
membrane
organisation
both
bacteria
animal
cells
level
lipid
bilayer.
This
essential
acid
can
however
be
other
interactions,
not
only
with
lipids,
partners,
that
are
crucial
understand
functional
roles
peptides.
review
focused
on
this
latter
less
known
describes
details,
qualitative
quantitative
ways:
(i)
physico-chemical
properties
Trp;
(ii)
effect
CPP
internalisation;
(iii)
importance
AMP
activity;
(iv)
interaction
AMPs
glycoconjugates
lipids
membranes
consequences
activity
peptides;
(v)
negatively
charged
polysaccharides
We
intend
bring
highlights
describe
extensive
possibilities
bilayer,
considered
cell
components,
carbohydrates
extracellular
matrix.
The
focus
will
allow
reader
reevaluate
reported
studies.
Altogether,
our
gathers
dedicated
studies
show
how
properties,
which
should
taken
into
account
design
future
expected
activity.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(10), P. 6773 - 6783
Published: Feb. 29, 2024
The
past
decade
has
seen
a
remarkable
growth
in
the
number
of
bioconjugation
techniques
chemistry,
biology,
material
science,
and
biomedical
fields.
A
core
design
element
technology
is
chemical
reaction
that
can
form
covalent
bond
between
protein
interest
labeling
reagent.
Achieving
chemoselective
aqueous
media
challenging,
especially
for
generally
less
reactive
amino
acid
residues,
such
as
tryptophan.
We
present
here
development
tryptophan-selective
methods
through
ultrafast
Lewis
acid-catalyzed
reactions
hexafluoroisopropanol
(HFIP).
Structure–reactivity
relationship
studies
have
revealed
combination
thiophene
ethanol
moieties
to
give
suitable
reagent
this
process,
which
enables
modification
peptides
proteins
an
extremely
rapid
unencumbered
by
noticeable
side
reactions.
capability
method
also
facilitated
radiofluorination
application
well
antibody
functionalization.
Enhancement
α-helix
HFIP
leads
its
compatibility
with
certain
protein,
report
demonstrates
further
stabilization
strategy
achieved
addition
ionic
liquid
medium.
nonaqueous
approaches
allow
access
numerous
are
unavailable
traditional
processes
will
advance
chemistry
proteins.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
61(7)
Published: Oct. 21, 2021
Hypervalent
iodine
compounds
are
powerful
reagents
for
the
development
of
novel
transformations.
As
they
exhibit
low
toxicity,
high
functional
group
tolerance,
and
stability
in
biocompatible
media,
have
been
used
functionalization
biomolecules.
Herein,
we
report
recent
advances
up
to
June
2021
peptide
protein
modification
using
hypervalent
reagents.
Their
use
as
transfer
or
oxidizing
is
discussed
this
Minireview,
including
methods
targeting
polar,
aromatic,
aliphatic
amino
acids
termini.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(41)
Published: Aug. 27, 2022
Abstract
As
the
aromatic
tryptophan
(Trp)
side
chain
plays
a
pivotal
role
in
influencing
structure
and
function
of
peptides
proteins,
it
has
become
an
attractive
target
for
late‐stage
modification
these
important
biomolecules.
Herein,
we
report
electrochemical
approach
functionalization
containing
Trp
through
manganese‐catalyzed
tandem
radical
azidation/heterocyclization.
This
oxidative
strategy
provides
access
to
azide‐substituted
tetrazolo[1,5‐
]indole‐containing
with
broad
functional
group
tolerance,
high
site
selectivity,
good
yields
products
(up
87
%)
under
mild
buffer
conditions.
Moreover,
modified
Trp‐containing
bearing
azide
functionality
are
promising
building
blocks,
paving
way
construction
various
derivatives,
such
as
“click”
chemistry
products.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(28), P. 11099 - 11107
Published: Jan. 1, 2024
An
unprecedented
tertiary
amine
catalyzed
peptide
allylation
between
Trp
and
MBH
carbonates
was
disclosed,
to
enable
late-stage
functionalization
macrocyclization
both
in
traditional
homogeneous
phase
on-resins
SPPS.
Chemical Communications,
Journal Year:
2021,
Volume and Issue:
57(47), P. 5758 - 5761
Published: Jan. 1, 2021
Mild
and
efficient
C–H
functionalization
of
tryptophan
tryptophan-containing
peptides
with
activated
α-bromo-carbonyl
compounds
under
visible-light
irradiation
is
described.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(41), P. 7577 - 7582
Published: Oct. 10, 2022
Here
we
report
a
general
C(sp3)–H/C(sp3)–H
dehydrogenative
coupling
strategy
for
the
preparation
of
various
natural
or
unnatural
amino
acids
from
readily
available
glycine
derivatives
and
hydrocarbons
through
combination
SET
HAT
process.
