Frontiers in Chemistry,
Journal Year:
2024,
Volume and Issue:
12
Published: May 6, 2024
A
series
of
C2-functionalied
Pt
(IV)
glycoconjugates
based
on
glucosamine
have
been
synthesised,
characterised
and
tested
as
anticancer
agents
a
different
2D
3D
cancer
cell
lines.
The
carbohydrate
will
act
targeted
delivery
system
to
improve
the
selectivity,
exploiting
Warburg
Effect
GLUTs
receptors
that
are
overexpressed
in
most
cells.
hydroxyl
at
C2
carbohydrates
does
not
participate
hydrogen
bonding
with
receptors,
making
an
attractive
position
for
drug
conjugation
seen
literature.
In
this
study,
we
use
amino
functionality
Copper-catalysed
Azide-Alkyne
Cycloaddition
“click”
(CuAAC)
reaction
connect
prodrug
scaffold
carbohydrate.
We
investigated
complexes
linker
lengths,
well
acetyl
protected
free
derivatives.
To
best
our
knowledge,
study
represents
first
glucosamine-conjugates
functionalised
C2.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(2), P. 514 - 518
Published: Jan. 5, 2021
The
cleavage
of
benzyl
ethers
by
catalytic
hydrogenolysis
or
Birch
reduction
suffers
from
poor
functional
group
compatibility
and
limits
their
use
as
a
protecting
group.
visible-light-mediated
debenzylation
disclosed
here
renders
temporary
protective
groups,
enabling
new
orthogonal
protection
strategies.
Using
2,3-dichloro-5,6-dicyano-1,4-benzoquinone
(DDQ)
stoichiometric
photooxidant,
can
be
cleaved
in
the
presence
azides,
alkenes,
alkynes.
reaction
time
reduced
hours
to
minutes
continuous
flow.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(18)
Published: Feb. 25, 2023
Herein,
we
describe
a
practical
protocol
for
the
removal
of
alcohol
functional
groups
through
reductive
cleavage
their
benzoate
ester
analogs.
This
transformation
requires
strong
single
electron
transfer
(SET)
reductant
and
means
to
accelerate
slow
fragmentation
following
substrate
reduction.
To
accomplish
this,
developed
photocatalytic
system
that
generates
potent
from
formate
salts
alongside
Brønsted
or
Lewis
acids
promote
reduced
intermediate.
deoxygenation
procedure
is
effective
across
structurally
electronically
diverse
alcohols
enables
variety
difficult
net
transformations.
no
precautions
exclude
air
moisture
remains
efficient
on
multigram
scale.
Finally,
can
be
adapted
one-pot
benzoylation-deoxygenation
sequence
enable
direct
deletion.
Mechanistic
studies
validate
role
acidic
additives
key
C(sp
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(18), P. 7669 - 7673
Published: Sept. 12, 2019
Photodecarboxylation-alkylation
of
conformationally
locked
monosaccharides
leads
to
inversion
stereochemistry
at
C5.
This
allows
the
synthesis
l-sugars
from
their
readily
available
d-counterparts.
Via
this
strategy,
methyl
l-guloside
was
synthesized
d-mannoside
in
21%
yield
over
six
steps.
Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(30), P. 11277 - 11290
Published: July 23, 2021
Few
classes
of
natural
products
rival
the
structural
audacity
oligosaccharides.
Their
complexity,
however,
has
stood
as
an
immense
roadblock
to
translational
research,
access
homogeneous
material
from
nature
is
challenging.
Thus,
while
carbohydrates
are
critical
myriad
functional
and
aspects
biological
sciences,
their
behavior
largely
descriptive.
This
challenge
presents
attractive
opportunity
for
synthetic
chemistry,
particularly
in
area
human
milk
science.
First,
there
inordinate
need
synthesizing
oligosaccharides
(HMOs).
Superimposed
on
this
goal
mission
conducting
syntheses
at
scale
enable
animal
studies.
Herein,
we
present
a
personalized
rumination
our
involvement,
that
colleagues,
which
led
synthesis
characterization
HMOs
mechanistic
probes.
Along
way,
highlight
chemical,
chemoenzymatic,
biology
based
approaches.
We
close
with
discussion
emergent
challenges
opportunities
synthesis,
broadly
defined,
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(14), P. 7637 - 7642
Published: Jan. 25, 2021
Abstract
Sucrose
is
the
main
saccharide
used
for
long‐distance
transport
in
plants
and
plays
an
essential
role
energy
metabolism;
however,
there
are
no
analogues
real‐time
imaging
live
cells.
We
have
optimised
a
synthetic
approach
to
prepare
sucrose
including
very
small
(≈50
Da
or
less)
Raman
tags
fructose
moiety.
Spectroscopic
analysis
identified
alkyne‐tagged
compound
6
as
analogue
recognised
by
endogenous
transporters
cells
with
higher
intensity
than
other
derivatives.
Herein,
we
demonstrate
application
of
first
optical
probe
visualise
uptake
intracellular
localisation
plant
using
microscopy.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(19), P. 12195 - 12205
Published: Sept. 23, 2022
Oligosaccharides,
either
as
such
or
part
of
glycolipids,
glycopeptides,
glycoproteins,
are
ubiquitous
in
nature
and
fulfill
important
roles
the
living
cell.
Also
medicine
to
some
extent
materials,
oligosaccharides
play
an
role.
In
order
study
their
function,
modifying
naturally
occurring
oligosaccharides,
building
reactive
groups
reporter
key
strategies.
The
development
drugs,
vaccines,
requires
introduction
subtle
modifications
structure
optimize
efficacy
and,
case
antibiotics,
circumvent
bacterial
resistance.
Provided
natural
oligosaccharide
is
available,
site-selective
modification
attractive
approach
total
synthesis
target
often
very
laborious.
Researchers
catalysis
areas,
transition-metal
catalysis,
enzyme
organocatalysis,
photoredox
have
made
considerable
progress
late-stage
methods
for
mono-
oligosaccharides.
It
foreseen
that
fields
enzymatic
glycans
chemical
(oligo)saccharides
will
potentially
meet
each
other,
but
there
a
lot
learn
discover
before
this
be
case.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(10), P. 6714 - 6722
Published: April 26, 2024
The
regioselective
modification
of
polyols
allows
rapid
access
to
their
derivatives,
thereby
accelerating
the
polyol-related
biology
and
drug
discovery.
We
previously
reported
that
benzoxaborole
is
a
potent
catalyst
for
containing
Chemical
1,1'-glycosylation
for
the
synthesis
of
non-reducing
disaccharides
is
complicated
by
need
to
simultaneously
control
stereochemistry
at
two
anomeric
centers.
While
considerable
progress
has
been
made
in
α,α-disaccharides,
assembly
1,1'-β,β-
and
1,1'-β,α-linked
sugars
received
comparatively
less
attention.
Many
naturally
occurring
their
biologically
active
mimetics
feature
asymmetrically
located
functional
groups
different
positions
on
pyranose
rings,
highlighting
demand
reliable
stereoselective
methods
synthesize
fully
orthogonally
protected
1,1'-conjugated
suitable
targeted
functionalisation
create
important
biomolecules.
By
exploiting
specific
electronic
torsional
effects
imposed
protecting
both
glycosyl
donor
lactol
acceptor
molecules,
we
achieved
highly
β,β-
β,α-1,1'-glycosylation
successfully
synthesised
a
library
β,α-linked
diglucosamines.
Our
approach
based
premise
that
reactivity
can
greatly
influence
stereochemical
outcome
glycosylation
reaction.
We
show
tailored
choice
orthogonal
alter
preferences
acceptors,
stabilising
conformations,
group-driven
modulation
nucleophilicity
useful
tool
achieve
1,1'-glycosidic
bond
formation.
Structure-activity
relationships
have
established
number
donor-lactol
pairs,
with
focus
optimizing
facilitate
1,1'-β,α-glycosylation
side
enhance
neighboring
stereoselectivity
side.
