On-Resin Selenopeptide Catalysts: Synthesis and Applications of Enzyme-Mimetic Reactions and Cyclization of Unsaturated Carboxylic Acids
Molecules,
Год журнала:
2025,
Номер
30(3), С. 480 - 480
Опубликована: Янв. 22, 2025
Selenium
reagents
are
useful
for
selenoenzyme-mimicking
reactions,
as
well
organic
synthesis.
However,
the
reaction
waste
containing
selenium
frequently
smells
unpleasant
and
exhibits
serious
toxicity.
Herein,
we
have
developed
new-type
on-resin
reagents,
H-UXX···-PAM
(5)
Ac-(X)U*XX···-PAM
(6),
where
U
U*
represent
selenocysteine
(U)
p-methoxybenzyl
(PMB)-protected
U,
respectively,
recyclable
catalysts,
in
which
U-containing
peptide
chains
linked
to
polystyrene
resin
PAM.
Synthesized
selenopeptides
5a–g
with
a
variable
amino
acid
sequence
were
evaluated
their
glutathione
peroxidase
(GPx)-like
activity
using
UV
1H
NMR
methods,
between
dithiothreitol
(DTTred)
H2O2
methanol.
It
was
found
that
intramolecular
interaction
basic
residue,
such
histidine
(H)
lysine
(K),
enhances
through
formation
of
an
NH···Se
hydrogen
bond.
On
other
hand,
catalytic
6a–d
oxidative
cyclization
β,γ-unsaturated
acids
(7)
into
α,β-unsaturated
lactones
(8).
Although
yield
8
significantly
decreased
after
second-
or
third-round
reaction,
due
detachment
moiety
from
resin,
results
demonstrated
reusability,
substrate
scope
6
catalyst.
Since
is
natural
acid,
potential
targets
novel-type
green
redox
catalysts.
Язык: Английский
Recent Advances in Selenium‐Mediated Redox Functional Group Interconversions
The Chemical Record,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 22, 2024
Abstract
The
conversion
of
a
functional
group
into
another
represents
the
core
organic
synthesis.
Within
arena
interconversions,
oxidative
and
reductive
transformations
occupy
privileged
position
development
new
sustainable,
selective,
general
methodologies
continue
to
attract
significant
interest.
Owing
versatility
their
chemistry,
selenium
compounds
offer
opportunities
achieve
both
oxidation
reduction
wide
range
groups.
Additionally,
possibility
generate
in
situ
active
oxidant
or
reducing
species
from
suitable
inert
precursors
enables
catalytic
processes.
In
this
review,
recent
advances
selenium‐mediated
with
particular
emphasis
on
cutting‐edge
researches
bringing
about
insights
comprehension
mechanistic
aspects,
will
be
discussed.
Язык: Английский