Oxazolidinone derivatives represent a class of important structures
in organic and medicinal chemistry, for example constituting
the
core structure of Evans’ auxiliaries for asymmetric synthesis
[1–3]
. This structural motif exists in a variety of natural products
and
active pharmaceutical species, such as the antidepressant drug
toloxatone,
the serotonin receptor agonist zolmitriptan, and the
muscle
relaxant metaxalone (Fig. 1) [4–6]. In particular, considerable
attention has been put on the development of compounds with
antibacterial
activity, where the oxazolidinone group of antibiotics
has
gained increasing interest [7–10]. For example, linezolid is a
lead
antibiotic against gram-positive bacteria that are resistant to
other
antibiotics [11–13].
Owing
to the importance of this heterocyclic structure, a variety
of synthetic methods to enantioenriched oxazolidinones have
been
developed and studied over the years [14–18]. In most of
these
approaches, the resulting enantiopurity emanates from chiral
starting
materials or through the action of transition metal catalysts.
Biocatalysis, however, one of the most efficient routes to
enantiopure
compounds, has not been applied in the direct synthesis
of these core structures. One reason for this has been the lack
identified enzymes that catalyze these processes. Compared to