DNA-Compatible N-Formylation of Amines by Using TMSCF2Br
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 15, 2025
DNA-encoded
libraries
(DELs)
have
emerged
as
powerful
tools
in
drug
discovery.
Protected
amino
acids
serve
essential
building
blocks
the
construction
of
DELs,
resulting
widespread
presence
groups
within
these
libraries.
N-formylation
free
amines
not
only
enhances
activity
lead
compounds
but
also
functions
an
effective
amino-protecting
strategy.
In
this
study,
we
introduce
trimethyl(bromodifluoromethyl)silane
(TMSCF2Br)
a
novel
reagent
for
DEL
synthesis.
This
approach
demonstrates
robustness
DEL-compatible
synthesis
and
enables
library
diversification
through
functional
group
transformation
(FGT).
Additionally,
achieved
efficient
removal
formyl
groups,
enabling
to
be
strategically
used
on-DNA
protection
orthogonal
Fmoc
Boc
groups.
Язык: Английский
On-DNA Three-Component Cycloaddition of Diazo Compounds, Nitrosoarenes, and Alkenes: Syntheses of Isoxazolidines for DNA-Encoded Chemical Libraries
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 25, 2024
A
DNA-compatible
three-component
reaction
is
disclosed
for
the
synthesis
of
on-DNA
polysubstituted
isoxazolidines
that
serve
as
privileged
core
scaffolds
in
numerous
natural
products
and
bioactive
molecules.
This
one-pot
approach
involves
1,3-dipolar
cycloaddition
DNA-tagged
styrenes
with
diazo
compounds
nitrosoarenes
an
aqueous
solution
KOAc.
The
demonstrates
excellent
functional
group
compatibility,
providing
a
conventional
protocol
construction
DNA-labeled
isoxazolidine
library.
Язык: Английский
The Furan–Thiol–Amine Reaction Facilitates DNA-Compatible Thiopyrrole-Grafted Macrocyclization and Late-Stage Amine Transformation
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 25, 2024
We
here
report
an
efficient
DNA-compatible
furan-thiol-amine
reaction
for
macrocyclization
and
late-stage
amine
transformation.
This
reaction,
conducted
under
mild
conditions,
enables
the
facile
cyclization
of
DNA-conjugated
linear
peptides
into
thiopyrrole-grafted
macrocycles
regardless
ring
size
or
side-chain
modification
with
good
to
excellent
conversion
yields.
Additionally,
this
strategy
was
employed
transformation
terminal
amines,
serving
as
critical
intermediates
in
construction
DNA-encoded
peptide
libraries.
Diverse
amines
were
successfully
converted
their
corresponding
thiopyrrole
scaffolds,
thereby
expanding
structural
diversity
that
can
be
achieved
within
Язык: Английский