Angewandte Chemie,
Год журнала:
2023,
Номер
135(43)
Опубликована: Июль 12, 2023
Abstract
Cyclodextrins
are
widely
used
as
carriers
of
small
molecules
for
drug
delivery
owing
to
their
remarkable
host
properties
and
excellent
biocompatibility.
However,
cyclic
oligosaccharides
with
different
sizes
shapes
limited.
Cycloglycosylation
ultra‐large
bifunctional
saccharide
precursors
is
challenging
due
the
constrained
conformational
spaces.
Herein
we
report
a
promoter‐controlled
cycloglycosylation
approach
synthesis
α‐(1→6)‐linked
mannosides
up
32‐mer.
thioglycosides
(
Z
)‐ynenoates
was
found
be
highly
dependent
on
promoters.
In
particular,
sufficient
amount
gold(I)
complex
played
key
role
in
proper
preorganization
transition
state,
providing
32‐mer
polymannoside,
which
represents
largest
synthetic
polysaccharide
date.
NMR
experiments
computational
study
revealed
that
2‐mer,
4‐mer,
8‐mer,
16‐mer,
adopted
states
shapes.
Abstract
The
opportunistic
human
pathogen
Pseudomonas
aeruginosa
is
the
causal
agent
of
a
wide
variety
infections.
This
non-fermentative
Gram-negative
bacillus
can
colonize
zones
where
skin
barrier
weakened,
such
as
wounds
or
burns.
It
also
causes
infections
urinary
tract,
respiratory
system
bloodstream.
P.
are
common
in
hospitalized
patients
for
which
multidrug-resistant,
respectively
extensively
drug-resistant
isolates
be
strong
contributor
to
high
rate
in-hospital
mortality.
Moreover,
chronic
cystic
fibrosis
especially
concerning,
since
very
tedious
treat.
exploits
diverse
cell-associated
and
secreted
virulence
factors,
play
essential
roles
its
pathogenesis.
Those
factors
encompass
carbohydrate-binding
proteins,
quorum
sensing
that
monitor
production
extracellular
products,
genes
conferring
extensive
drug
resistance,
secretion
deliver
effectors
kill
competitors
subvert
host
functions.
In
this
article,
we
highlight
recent
advances
understanding
pathogenicity
well
efforts
identification
new
targets
development
therapeutic
strategies
against
These
provide
innovative
promising
circumvent
infection
caused
by
important
pathogen.
Expert Review of Vaccines,
Год журнала:
2023,
Номер
22(1), С. 1055 - 1078
Опубликована: Окт. 30, 2023
Introduction
Antimicrobial
resistance
(AMR)
is
responsible
for
the
death
of
millions
worldwide
and
stands
as
a
major
threat
to
our
healthcare
systems,
which
are
heavily
reliant
on
antibiotics
fight
bacterial
infections.
The
development
vaccines
against
main
pathogens
involved
urgently
required
prevention
remains
essential
rise
AMR.
Organic Letters,
Год журнала:
2022,
Номер
24(51), С. 9479 - 9484
Опубликована: Дек. 16, 2022
Nucleoside
analogues
are
widely
used
as
anticancer
and
antiviral
drugs.
Here,
we
develop
a
highly
efficient
gold(I)-catalyzed
N-glycosylation
approach
for
versatile
synthesis
of
various
types
nucleosides
deoxynucleosides
with
glycosyl
(Z)-ynenoates
donors.
The
wide
scope
the
was
demonstrated
by
31
pyrimidine
8
purine
nucleosides.
Remarkably,
pyranosyl
purines
found
to
be
very
effective
regioselective
N9
Based
on
catalytic
approach,
convenient
two
5'-deoxynucleosides
drugs
(capecitabine
galocitabine),
four
2'-deoxynucleoside
(floxuridine,
trifluridine,
decitabine
cladribine),
3',5'-dideoxynucleoside
analogues,
2',5'-dideoxynucleoside
achieved
in
collective
manner.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(43)
Опубликована: Июль 12, 2023
Cyclodextrins
are
widely
used
as
carriers
of
small
molecules
for
drug
delivery
owing
to
their
remarkable
host
properties
and
excellent
biocompatibility.
However,
cyclic
oligosaccharides
with
different
sizes
shapes
limited.
Cycloglycosylation
ultra-large
bifunctional
saccharide
precursors
is
challenging
due
the
constrained
conformational
spaces.
Herein
we
report
a
promoter-controlled
cycloglycosylation
approach
synthesis
α-(1→6)-linked
mannosides
up
32-mer.
thioglycosides
(Z)-ynenoates
was
found
be
highly
dependent
on
promoters.
In
particular,
sufficient
amount
gold(I)
complex
played
key
role
in
proper
preorganization
transition
state,
providing
32-mer
polymannoside,
which
represents
largest
synthetic
polysaccharide
date.
NMR
experiments
computational
study
revealed
that
2-mer,
4-mer,
8-mer,
16-mer,
adopted
states
shapes.
ACS Central Science,
Год журнала:
2024,
Номер
10(8), С. 1515 - 1523
Опубликована: Июль 10, 2024
is
one
of
the
leading
causes
nosocomial
infections
and
has
become
increasingly
resistant
to
multiple
antibiotics.
However,
development
novel
classes
antibacterial
agents
against
multidrug-resistant
Current Opinion in Chemical Biology,
Год журнала:
2023,
Номер
78, С. 102418 - 102418
Опубликована: Дек. 21, 2023
Exopolysaccharides
are
produced
and
excreted
by
bacteria
in
the
generation
of
biofilms
to
provide
a
protective
environment.
These
polysaccharides
generally
generated
as
heterogeneous
polymers
varying
length,
featuring
diverse
substitution
patterns.
To
obtain
well-defined
fragments
these
polysaccharides,
organic
synthesis
often
is
method
choice,
it
allows
for
full
control
over
chain
length
installation
pre-determined
pattern.
This
review
presents
several
recent
syntheses
exopolysaccharide
Pseudomonas
aeruginosa
Staphylococcus
aureus
illustrates
how
have
been
used
study
biosynthesis
enzymes
generate
synthetic
glycoconjugate
vaccines.
JACS Au,
Год журнала:
2025,
Номер
5(4), С. 1903 - 1913
Опубликована: Апрель 16, 2025
Bordetella
hinzii
is
a
zoonotic
pathogen,
which
can
cause
brain
abscess,
pneumonia,
bacteremia,
and
urinary
tract
infection.
Vaccines
are
economical
effective
means
for
combating
infectious
diseases.
Herein,
we
present
the
first
total
synthesis
of
highly
functionalized
mono-
oligosaccharides
B.
O-antigen
vaccine
development.
The
rare
2,3-diacetamidopyranoses
were
generated
from
3-O-acetyl-2-nitroglycals
via
an
organocatalyzed
one-pot
relay
glycosylation
method.
postglycosylation
oxidation
strategy
was
used
to
overcome
poor
reactivity
2,3-diacetamido-aldouronic
acid
building
blocks
in
reactions.
Direct
amidation
alduronic
with
NH3
late
stage
reduced
protecting
group
operation
increased
synthetic
efficiency.
Di-tert-butylsilylidene-directed
α-galactosylation
method
construct
challenging
1,2-cis-glycosidic
bond.
Six
obtained
further
conjugated
human
serum
albumin
antigenicity
evaluation
(the
sera
antibodies
vaccinated
mouse
inactivated
hinzii).
terminal
tetrasaccharide
has
been
identified
as
potential
glycol-epitope
might
be
useful
development
against
hinzii.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
Comprehensive
Summary
Pseudomonas
aeruginosa
is
an
opportunistic
pathogen
responsible
for
cystic
fibrosis,
bloodstream
infections
and
hospital‐acquired
pneumonia.
The
O‐antigen
of
lipopolysaccharide
on
the
cell
surface
P.
has
been
identified
as
a
promising
target
development
carbohydrate‐based
vaccines.
In
this
study,
we
present
first
total
synthesis
tetrasaccharide
repeating
unit
serotype
4
using
linear
[((1+1)+1)+1]
glycosylation
strategy.
All
rare
amino
sugars
were
synthesized
from
commercially
available
monosaccharides.
formation
1,2‐
cis
L‐fucosamine
glycosidic
bonds
was
achieved
with
high
efficiency
stereoselectivity
by
judicious
choice
C3/C4‐OH
protecting
groups
L‐fucosamine.
N
‐phenyl
trifluoroacetimidate
glycosyl
donors
have
proven
to
be
more
efficient
than
selenoglycoside
or
thioglycoside
during
glycosylation,
particularly
when
coupling
low‐reactivity
C3‐OH
group
O4‐Bz
protected
L‐FucN
3
acceptor.
TBSOTf
demonstrated
higher
efficacy
catalyst
compared
TMSOTf
promoting
less
reactive
acceptors.
synthetic
O‐antigen,
which
incorporates
pentyl
amine
linker
at
reducing
end,
prepared
conjugation
carrier
proteins
utilization
in
microarray
studies
aimed
further
immunological
investigations.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(19), С. 3986 - 3994
Опубликована: Янв. 1, 2024
Sulfated
mannuronate
glycans
with
up
to
17
sulfation
sites
were
synthesized
using
a
microwave-assisted
approach
and
evaluated
as
inhibitors
against
SARS-CoV-2.
National Science Review,
Год журнала:
2024,
Номер
11(10)
Опубликована: Авг. 23, 2024
ABSTRACT
Cold-adapted
species
are
able
to
generate
cryoprotective
proteins
and
glycoproteins
prevent
freezing
damage.
The
[→4)-β-D-Manp-(1→4)-β-D-Xylp-(1→]n
xylomannan
from
the
Alaska
beetle
Upis
ceramboides
was
disclosed
by
Walters
co-workers
in
2009
as
first
glycan-based
antifreeze
agent,
which
later
reported
be
found
diverse
taxa.
Here,
we
report
rapid
synthesis
of
four
types
xylomannans,
including
proposed
up
a
64-mer
(Type
I),
regioisomeric
[→3)-β-D-Manp-(1→4)-β-D-Xylp-(1→]n
16-mer
II),
diastereomeric
[→4)-β-L-Manp-(1→4)-β-D-Xylp-(1→]n
III)
block-wise
[→4)-β-D-Manp-(1→]m[→4)-β-D-Xylp-(1→]n
32-mer
IV),
employing
strategic
iterative
exponential
glycan
growth
(IEGG)
process.
nuclear
magnetic
resonance
spectral
data
alleged
natural
accordance
only
those
Type
IV
none
these
synthetic
xylomannans
has
been
capable
inducing
thermal
hysteresis.
These
results
disprove
previous
reports
about
occurrence
xylomannans.
