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betaDarabinofuranosyl

Beta-D-arabinofuranosyl, often written betaDarabinofuranosyl, refers to the beta anomer of the five-membered furanose form of the monosaccharide D-arabinose. In biochemistry and medicinal chemistry, the term denotes the sugar moiety that forms the core of nucleosides and nucleotides when attached to a nucleobase via a beta glycosidic bond at the anomeric carbon (C1′).

Chemical and stereochemical characteristics: The arabinofuranose sugar adopts a furanose ring, and its configuration at the

Biological roles and occurrences: Beta-D-arabinofuranose residues occur in certain natural polysaccharides, including components of plant and

Nomenclature and usage: The term emphasizes both the stereochemistry (beta) and the sugar identity (D-arabinofuranose) and

C2′
and
C3′
positions
differs
from
that
of
ribose.
In
beta-D-arabinofuranosyl
nucleosides,
the
glycosidic
linkage
to
the
base
is
in
the
beta
orientation,
which
affects
the
sugar’s
three-dimensional
shape
and
how
it
is
recognized
by
enzymes
and
other
proteins.
bacterial
cell
walls
such
as
arabinogalactan.
In
medicine,
beta-D-arabinofuranosyl
nucleosides
are
important
scaffolds;
several
anticancer
and
antiviral
agents
use
this
sugar,
including
cytarabine
(Ara-C)
and
vidarabine
(ara-A),
where
the
arabinose
sugar
is
linked
to
a
nucleobase
in
the
beta
configuration.
is
used
when
describing
nucleosides
such
as
beta-D-arabinofuranosyladenine,
cytidine,
or
guanine
derivatives.
The
concept
underpins
the
study
of
arabinose-containing
glycoconjugates
and
the
design
of
sugar-modified
nucleosides
in
medicinal
chemistry.