Carbohydrates
represent
the
most
structurally
diverse
class
of
biopolymers
and
are
crucially
involved
in
a
plethora
biochemical
biological
processes
essential
for
every
form
life.
In
particular,
bacterial
surface
polysaccharides
(
PSs
)
can
trigger
adhesion
host
cells
infection;
hence,
they
key
virulence
factors.
The
seminal
finding
that
carbohydrate-specific
antibodies
predominantly
responsible
protection
against
bacteria
is
basis
carbohydrate-based
vaccines
development.
Among
them,
glycoconjugate
vaccines,
based
on
pathogen-related
poly-
or
oligosaccharides
chemically
conjugated
to
an
immunogenic
protein
carrier,
formidable
weapon
protect
public
health.
Despite
their
great
success,
currently,
licensed
suffer
from
several
drawbacks,
which
still
pose
strong
limitations
wider
use
massive
vaccination
campaigns.
There
is,
therefore,
urgent
call
development
improved
vaccine
constructs
with
well-defined
compositions
more
cost-effective
production
processes.
design
innovative
carbohydrate
takes
advantage
cutting-edge
technologies
developed
over
last
decade,
it
steered
by
recent
advances
modern
immunology.
this
chapter,
mechanism
action
characteristics
each
major
component
illustrated.
addition,
we
report
account
currently
investigated
improve
existing
as
well
novel
able
timely
combat
emerging
infectious
diseases
and/or
address
unmet
medical
needs.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(64)
Опубликована: Авг. 28, 2023
Abstract
Human
milk
oligosaccharides
(HMO)
have
emerged
as
a
very
active
area
of
research
in
glycoscience
and
nutrition.
HMO
are
involved
the
early
development
infants
may
help
to
prevent
certain
diseases.
The
chemical
methods
for
obtaining
individual
aids
global
effort
dedicated
understanding
roles
these
biomolecules.
Reported
herein
is
synthesis
two
common
core
hexasaccharides
found
human
milk,
i.
e.
para
‐lacto‐
N
‐hexaose
(
p
LNH)
‐neohexaose
LNnH).
After
screening
multiple
leaving
groups
temporary
protecting
group
combinations,
3+3
convergent
coupling
strategy
was
work
best
linear
glycans.
Beilstein Journal of Organic Chemistry,
Год журнала:
2023,
Номер
19, С. 1015 - 1020
Опубликована: Июль 6, 2023
Automated
glycan
assembly
(AGA)
affords
collections
of
well-defined
glycans
in
a
short
amount
time.
We
systematically
analyzed
how
parameters
connected
to
the
solid
support
affect
AGA
outcome
for
three
different
sequences.
showed
that,
while
loading
and
reaction
scale
did
not
significantly
influence
outcome,
chemical
nature
linker
dramatically
altered
isolated
yields.
identified
that
major
determinants
yields
are
cleavage
from
post-AGA
purification
steps.
Angewandte Chemie,
Год журнала:
2021,
Номер
133(22), С. 12521 - 12531
Опубликована: Фев. 26, 2021
Abstract
The
stereoselectivity
and
yield
in
glycosylation
reactions
are
paramount
but
unpredictable.
We
have
developed
a
database
of
acceptor
nucleophilic
constants
(Aka)
to
quantify
the
nucleophilicity
hydroxyl
groups
influenced
by
steric,
electronic
structural
effects,
providing
connection
between
experiments
computer
algorithms.
subtle
reactivity
differences
among
on
various
carbohydrate
molecules
can
be
defined
Aka,
which
is
easily
accessible
simple
convenient
automation
system
assure
high
reproducibility
accuracy.
A
diverse
range
donors
acceptors
with
well‐defined
promoters
were
organized
processed
designed
software
program
“GlycoComputer”
for
prediction
without
involving
sophisticated
computational
processing.
importance
Aka
was
further
verified
random
forest
algorithm,
applicability
tested
synthesis
Lewis
skeleton
show
that
accurately
estimated.
Synthesis,
Год журнала:
2022,
Номер
55(09), С. 1337 - 1354
Опубликована: Сен. 7, 2022
Abstract
Solid-phase
glycan
synthesis
(SPGS)
is
a
valuable
approach
to
access
broad
collections
of
complex,
well-defined
oligo-
and
polysaccharides
in
short
amounts
time.
The
target
structure
assembled
following
iterative
cycles
glycosylation
deprotection,
often
aided
by
automated
machines.
To
expand
the
scope
SPGS,
new
solid
supports,
linkers,
deprotection
reactions,
functionalization
strategies
are
constantly
being
developed.
Here
we
discuss
state
art
with
particular
focus
on
chemistry
happening
solid-phase.
We
highlight
recent
achievements
as
well
challenges
be
addressed
SPGS
even
further.
1
Introduction
2
Solid-Phase
Glycan
Synthesis
2.1
Solid
Support
2.2
Linker
2.3
Assembly
Process
2.4
Post-Assembly
Manipulations
2.5
Analysis
2.6
Cleavage
from
3
Conclusion
Outlook
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(50), С. 22456 - 22459
Опубликована: Авг. 28, 2020
Automated
chemical
oligosaccharide
synthesis
is
an
attractive
concept
that
has
been
successfully
applied
to
a
large
number
of
target
structures,
but
requires
excess
quantities
suitably
protected
and
activated
building
blocks.
Herein
we
demonstrate
the
use
biocatalysis
supply
such
reagents
for
automated
synthesis.
By
using
promiscuous
NmLgtB-B
β1-4
galactosyltransferase
from
Neisseria
meningitidis
fast
robust
access
LacNAc
motif,
common
many
cell-surface
glycans,
starting
either
lactose
or
sucrose
as
glycosyl
donors.
The
enzymatic
product
was
shown
be
incorporated
complete
unit
into
tetrasaccharide
by
assembly.
Chemical Communications,
Год журнала:
2021,
Номер
58(5), С. 641 - 644
Опубликована: Дек. 8, 2021
Gold-catalyzed
synthesis
of
oligosaccharides
is
reported
by
solid-phase
methods.
The
utility
this
demonstrated
the
branched
and
linear
pentaarabinofuranosides.
