Beilstein Journal of Organic Chemistry,
Год журнала:
2025,
Номер
21, С. 1104 - 1115
Опубликована: Июнь 4, 2025
Pipecolic
acid
is
known
as
a
non-proteinogenic
amino
with
secondary
amine.
It
contains
six-membered
ring
and
is,
like
its
five-membered
correlate,
for
structure
inducing
properties,
which
are
particularly
useful
in
the
design
of
peptide
conformations.
We
present
new
improved
way
to
generate
enantiomerically
pure
pipecolic
derivatives
aryl
modifications
C
6
position
by
utilising
chiral
pool
combination
transition
metal-catalysed
cross-coupling
reactions.
Moreover,
we
an
in-depth
NMR
analysis
key
intermediate
steps,
illustrates
conformational
constraints
accordance
coupling
constants
resulting
dihedral
angles.
ACS Medicinal Chemistry Letters,
Год журнала:
2023,
Номер
14(5), С. 557 - 565
Опубликована: Апрель 24, 2023
Life
is
constructed
primarily
using
a
toolbox
of
20
canonical
amino
acids─relying
upon
these
building
blocks
for
the
assembly
proteins
and
peptides
that
regulate
nearly
every
cellular
task,
including
cell
structure,
function,
maintenance.
While
Nature
continues
to
be
source
inspiration
drug
discovery,
medicinal
chemists
are
not
beholden
only
acids
have
begun
explore
non-canonical
(ncAAs)
construction
designer
with
improved
drug-like
properties.
However,
as
our
ncAAs
expands,
hunters
encountering
new
challenges
in
approaching
iterative
peptide
design–make–test–analyze
cycle
seemingly
boundless
set
blocks.
This
Microperspective
focuses
on
technologies
accelerating
ncAA
interrogation
discovery
(including
HELM
notation,
late-stage
functionalization,
biocatalysis)
while
shedding
light
areas
where
further
investment
could
accelerate
medicines
but
also
improve
downstream
development.
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 26, 2024
Cross-electrophile
coupling
(XEC),
defined
by
us
as
the
cross-coupling
of
two
different
σ-electrophiles
that
is
driven
catalyst
reduction,
has
seen
rapid
progression
in
recent
years.
As
such,
this
review
aims
to
summarize
field
from
its
beginnings
up
until
mid-2023
and
provide
comprehensive
coverage
on
synthetic
methods
current
state
mechanistic
understanding.
Chapters
are
split
type
bond
formed,
which
include
C(sp
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(20), С. 10930 - 10937
Опубликована: Май 15, 2023
Amines
and
carboxylic
acids
are
abundant
synthetic
building
blocks
that
classically
united
to
form
an
amide
bond.
To
access
new
pockets
of
chemical
space,
we
interested
in
the
development
amine-acid
coupling
reactions
complement
coupling.
In
particular,
formation
carbon-carbon
bonds
by
formal
deamination
decarboxylation
would
be
impactful
addition
synthesis
toolbox.
Here,
report
a
cross-coupling
alkyl
amines
aryl
C(sp
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(23), С. 16306 - 16313
Опубликована: Май 28, 2024
Transaminases
are
choice
biocatalysts
for
the
synthesis
of
chiral
primary
amines,
including
amino
acids
bearing
contiguous
stereocenters.
In
this
study,
we
employ
lysine
as
a
"smart"
amine
donor
in
transaminase-catalyzed
dynamic
kinetic
resolution
reactions
to
access
β-branched
noncanonical
arylalanines.
Our
mechanistic
investigation
demonstrates
that,
upon
transamination,
lysine-derived
ketone
byproduct
readily
cyclizes
six-membered
imine,
driving
equilibrium
desired
direction
and
thus
alleviating
need
load
superstoichiometric
quantities
or
deploy
multienzyme
cascade.
Lysine
also
shows
good
overall
compatibility
with
panel
wild-type
transaminases,
promising
hint
its
application
smart
more
broadly.
Indeed,
by
approach,
furnished
broad
scope
arylalanines,
some
hitherto
intractable
cyclopropyl
isopropyl
substituents,
high
yields
excellent
selectivities.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(40), С. 27583 - 27593
Опубликована: Сен. 26, 2024
The
exploration
of
strong
chemical
bonds
as
synthetic
handles
offers
new
disconnection
strategies
for
the
synthesis
functionalized
molecules
via
transition
metal
catalysis.
However,
slow
oxidative
addition
rate
these
covalent
to
a
center
hampers
their
utility.
Here,
we
report
C(sp
ACS Catalysis,
Год журнала:
2023,
Номер
13(14), С. 9336 - 9345
Опубликована: Июнь 28, 2023
An
electrochemical,
nickel-catalyzed
reductive
coupling
of
alkylpyridinium
salts
and
aryl
halides
is
reported.
High-throughput
experimentation
(HTE)
was
employed
for
rapid
reaction
optimization
evaluation
a
broad
scope
pharmaceutically
relevant
structurally
diverse
halides,
including
complex
drug-like
substrates.
In
addition,
the
transformation
compatible
with
both
primary
secondary
distinct
conditions.
Mechanistic
insights
were
critical
to
enhance
efficiency
using
salts.
Systematic
comparisons
electrochemical
non-electrochemical
methods
revealed
complementary
two
approaches.
