Expanding the Reach of Sustainable Solid-Phase Peptide Synthesis: One-Pot, Metal-Free Alloc Removal–Peptide Coupling
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 17, 2025
While
the
allyloxycarbonyl
(Alloc)
protecting
group
has
played
a
key
role
in
solid-phase
peptide
synthesis
(SPPS),
providing
access
to
wide
range
of
peptides,
its
removal
suffered
from
relying
on
air-sensitive
Pd(0)
complexes
hazardous
solvents.
We
report
metal-free,
on-resin
Alloc
using
readily
available
iodine/water
environmentally
sensible
PolarClean
(PC)/ethyl
acetate
(EtOAc)
carried
out
one-pot
manner
with
racemization-free
couplings
employing
both
9-fluorenylmethoxycarbonyl
(Fmoc)
and
amino
acids
(AAs).
SPPS
been
demonstrated
by
performing
consecutive
removals–peptide
couplings,
whereas
compatibility
long
peptides
proven
carrying
an
removal–coupling
39
AA
resin.
Upscaling
10
g
was
combined
TFA-free
resin
cleavage,
opening
up
opportunities
for
Alloc-AAs
as
synthons
sustainable
manufacturing.
Язык: Английский
A Sustainable Chemo-Enzymatic Approach to the Synthesis of Liraglutide
ACS Sustainable Chemistry & Engineering,
Год журнала:
2024,
Номер
12(45), С. 16791 - 16799
Опубликована: Ноя. 1, 2024
The
development
of
green
approaches
to
peptide
synthesis
is
essential,
as
peptides
are
gaining
prominence
in
the
pharmaceutical
market.
Traditional
methods
often
involve
harmful
solvents
and
high
energy
use,
prompting
a
shift
toward
sustainable
eco-friendly
alternatives.
Liraglutide,
GLP-1
analogue
used
treatment
obesity
type-2
diabetes,
has
been
synthesized
through
hybrid
chemo-enzymatic
approach
(CEPS),
taking
advantage
solvent
mixtures
fragments
selectivity
ligase
enzyme
for
their
coupling.
This
method
offers
great
advantages
both
quality
upstream
wastes
reduction
volumes
downstream
purification,
together
with
purity
target
liraglutide.
Язык: Английский