Controlled Synthesis of Polymers†
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(10), С. 1235 - 1248
Опубликована: Фев. 14, 2023
Comprehensive
Summary
Controlled
synthesis
is
central
to
obtaining
polymers
with
accurate
structures
and
excellent
performances.
Recent
research
in
the
controlled
of
has
focused
on
optimizing
monomers,
initiation
systems,
reaction
conditions.
The
satisfactory
sequence,
topological
structure,
dispersity
have
been
achieved
satisfy
growing
demand
for
functional
polymers.
This
review
summarizes
selection
monomers
various
types
structures,
innovation
optimization
conditions
discusses
their
challenges
opportunities.
Язык: Английский
Promoter‐Controlled Synthesis and Conformational Analysis of Cyclic Mannosides up to a 32‐mer
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.
Язык: Английский
Enzymatic Production of Low-Molecular-Weight Hyaluronan and Its Oligosaccharides: A Review and Prospects
Journal of Agricultural and Food Chemistry,
Год журнала:
2022,
Номер
70(44), С. 14129 - 14139
Опубликована: Окт. 27, 2022
Hyaluronic
acid
(HA)
is
a
nonsulfated
linear
glycosaminoglycan
with
negative
charge.
Different
from
the
high-molecular-weight
HAs,
low-molecular-weight
HAs
(LMW-HAs,
4–120
kDa)
and
hyaluronan
oligosaccharides
(O-HAs,
<4
exhibit
certain
unique
biological
properties,
owing
to
which
these
have
wide
range
of
applications
in
field
medicine.
However,
chemical
synthesis
high-purity
LMW-HAs
O-HAs
requires
complex
procedures,
renders
this
process
difficult
achieve.
The
degradation
HA
achieved
under
catalysis
hyaluronidases.
In
recent
years,
various
hyaluronidase
genes
been
identified,
their
enzymatic
properties
analyzed.
context,
present
review
summarizes
hyaluronidases
different
sources,
characterized.
focuses
on
crystal
structure
catalytic
mechanism
underlying
addition,
molecular
weight
distributions
preparation
approaches
products
are
described.
general
orientation
research
was
speculated
based
existing
literature.
Accordingly,
efficient
large-scale
production
using
green
approach
anticipated.
Язык: Английский
Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 16, 2024
Comprehensive
Summary
Traditional
protecting
groups
are
often
removed
under
harsh
conditions
with
potentially
hazardous
reagents,
thereby
impeding
the
convenient
synthesis
of
oligosaccharides
and
glycosides.
Herein,
we
present
to
utilize
photolabile
ortho
‐nitro‐benzyl
carbonate
(
o
NBC)
as
a
permanent
hydroxyl
group
for
stereocontrolled
The
Ph
3
PO‐modulated
glycosylation
strongly
disarmed
per‐
O
‐
NBC‐protected
glycosyl
ynenoates
preferred
afford
glycosides
excellent
α‐selectivities
via
β‐phosphonium
transition
state.
Based
on
NBC‐mediated
galactosylation,
glycolipid
digalactosyl
diacylglycerol
(DGDG)
containing
six
double
bonds
two
esters
was
achieved
in
straightforward
manner.
Язык: Английский
Stereodirecting Effects of 4‐O‐ortho‐cyanobenzyl Ether on Chemical Glycosylation with Glucopyranosyl Donor
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
41(6), С. 651 - 656
Опубликована: Ноя. 16, 2022
Comprehensive
Summary
Here
we
report
a
systematic
investigation
on
the
stereodirecting
effects
of
4‐
O
‐
ortho
‐cyanobenzyl
ether
(
o
BCN)
group
with
glucopyranosyl
donor.
Experimental
studies
revealed
that
glycosylation
reactions
using
this
donor
generally
show
dual‐stereoselectivities
depending
acceptor
nucleophilicity,
is,
weak
nucleophile
acceptors
affords
α‐glycosides
specifically
while
strong
β‐glycosides
preferentially.
DFT
computations
suggested
nucleophiles
preferentially
attack
predominant
covalent
α‐glycosyl
triflate
intermediate
in
an
S
N
2‐like
manner,
less
stable
and
more
reactive
β‐glycosyl
H‐bond
mediated
direction.
The
first
facile
synthesis
hexasaccharide
repeating
unit
serotype
IV
B
Streptococcus
capsular
polysaccharide
demonstrated
versatile
utility
glucosyl
building
blocks
BCN
functionality
carbohydrate
chemistry.
Язык: Английский
Development of Recyclable Polystyrene-Supported Phosphonic Acid Resins for Carbohydrate Immobilization and Glycosylation
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(23), С. 16467 - 16484
Опубликована: Ноя. 9, 2023
This
article
describes
the
development
of
a
recyclable
polystyrene-based
phosphonic
acid
resin
and
its
use
for
synthesis
immobilized
glycosyl
phosphonate
donors
subsequent
glycosylation
reaction.
solid
support
was
generated
on
decagram
scale
from
commercially
available
Merrifield
subsequently
functionalized
via
two
different
methods
into
eight
glycosylphosphonates.
The
resultant
glycosylphosphonate-containing
resins
were
obtained
in
59–96%
yields
found
to
be
bench-stable
at
room
temperature.
These
could
activated
using
trifluoroborane
etherate
80
°C
react
with
various
alcohol-
thiol-based
acceptors
provide
17
glycosides
good-to-excellent
(53–98%).
In
addition,
it
demonstrated
that
glycosylated
recovered
recycled
multiple
times
regenerate
glycosylphosphonate
subjected
on-resin
glycan
elongation.
Язык: Английский
Chemical Synthesis of an Octasaccharide Derivative Related to Group B StreptococcusCell‐Wall Polysaccharide
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
41(2), С. 151 - 158
Опубликована: Окт. 3, 2022
Comprehensive
Summary
Group
B
Streptococcus
(GBS)
is
the
major
pathogen
that
causes
invasive
infectious
diseases
in
neonates
and
infants.
The
development
of
preventive
therapeutic
strategies
against
GBS
infection
has
been
becoming
most
pressing
subject
worldwide.
carbohydrate
(GBC),
group
B‐specific
polysaccharide
distinguishes
with
other
streptococci
species,
identified
as
an
attractive
antigen
for
diagnosis
vaccine
because
its
highly
conservative
tetra‐antennary
structure.
In
this
paper,
a
convergent
[3
+
5]
glycosylation
strategy
efficient
synthesis
octasaccharide
derivative
related
to
GBC
oligosaccharide
unit
II
developed.
synthesis,
each
reaction
was
efficiently
constructed
glycosyl
imidates,
especially
trifluoroacetimidate,
donors,
glycosidic
bond
stereoselectively
controlled
via
neighboring
participation
effect
acyl
on
2‐
O
‐position
imidate
donors
or
solvent
Et
2
O.
Furthermore,
aminoethylphosphate
smoothly
installed
6‐
d
‐glucitol
residue
using
phosphoramidite
method.
After
global
deprotection,
target
successfully
obtained
from
29
steps
overall
yield
1.37%.
free
amino
spacer
molecule
enables
modification
functionalized
biomolecules
further
biological
studies.
Язык: Английский
Stereoselective synthesis of α-glucosides with glucosyl (Z)-Ynenoates as donors
Carbohydrate Research,
Год журнала:
2022,
Номер
523, С. 108710 - 108710
Опубликована: Окт. 31, 2022
Язык: Английский
Promoter‐Controlled Synthesis and Conformational Analysis of Cyclic Mannosides up to a 32‐mer
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.
Язык: Английский