One-Pot Stereoselective Synthesis of C-Glycosyl Amino Acids with Vicinal Stereocenters
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
A
palladium-catalyzed
cascade
coupling
between
glycals
and
racemic
α-nitroesters
enables
the
stereoselective
construction
of
C-glycosyl
amino
acids
bearing
two
contiguous
stereocenters,
achieving
dual
stereocontrol
(exclusive
β-C1,
up
to
10:1
diastereomeric
ratio
at
C7).
This
one-pot
protocol
room
temperature
accommodates
diverse
substrates
(25
examples).
Mechanistic
studies
demonstrate
that
decarboxylation-induced
C4-oxyanion
directs
1,4-syn
selectivity,
while
steric
modulation
governs
C7
stereochemistry.
Synthetic
versatility
is
evidenced
by
gram-scale
synthesis
late-stage
functionalization
trihydroxy
C-glycosides,
2,3-dideoxy
sugars,
4-O-amino
acid
conjugates.
Язык: Английский
Structure‐based virtual screening aids the identification of glycosyltransferases in the biosynthesis of salidroside
Plant Biotechnology Journal,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 11, 2025
Summary
Glycosylation
plays
an
important
role
in
the
structural
diversification
of
plant
natural
products.
The
identification
efficient
glycosyltransferases
is
also
a
crucial
step
for
biosynthesis
valuable
glycoside
However,
functional
characterization
(GTs)
from
extensive
gene
list
labour‐intensive
and
challenging.
Salidroside
bioactive
component
derived
plants,
widely
utilized
fields
food
medicine.
Here,
through
transcriptome
analysis
structure‐based
virtual
screening,
we
identified
two
GTs
that
participated
salidroside
rarely
studied
herbaceous
plant,
Astilbe
chinensis
.
Ach15909
was
found
to
possess
high
catalytic
activity
as
evidenced
by
determination
its
parameters.
key
residues
determine
were
further
determined.
Additionally,
shows
preference
substrates
with
volume
<150
Å
3
,
replacing
interdomain
linker
region
located
between
N‐
C‐terminal
domains
allows
it
accept
previously
not
catalyzable.
Overall,
screening
approach
showed
efficiency
cost‐effectiveness;
successful
glycosylation
sheds
light
on
uncovering
additional
enzymes
forthcoming
research.
Язык: Английский
Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals
Liu Xingle,
Qiu-Qi Mu,
Li Xu
и другие.
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 22, 2024
Following
the
satisfactory
catalytic
performance
of
cobalt
in
Язык: Английский
ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations
Molecules,
Год журнала:
2024,
Номер
29(19), С. 4710 - 4710
Опубликована: Окт. 4, 2024
An
efficient
and
versatile
glycosylation
methodology
is
crucial
for
the
systematic
synthesis
of
oligosaccharides
glycoconjugates.
A
direct
intermolecular
an
indirect
intramolecular
have
been
developed,
former
can
be
applied
to
medium-to-long-chain
glycans
like
that
nucleotides
peptides.
The
development
a
generally
applicable
approach
stereoselective
construction
glycosidic
bonds
remains
major
challenge,
especially
1,2-
Язык: Английский