1 research outputs found
Highly Efficient One-Pot Multienzyme Cascades for the Stereoselective Synthesis of Natural Naphthalenones
Herein, a biocatalytic cascade containing an ene-reductase
(NostocER)
and naphthol reductase (tetrahydroxynaphthalene or trihydroxynaphthalene
reductase) of Magnaporthe grisea and
NADPH is developed. The optimized multienzyme cascade is applied for
the one-pot reduction of plumbagin to obtain biologically active cis-(3R,4R)-isoshinanolone,
with drcis:trans 98:2 and >99% ee in
96%
yield. Furthermore, naturally occurring (+)-isosclerone, (+)-shinanolone,
(−)-shinanolone, and (S)-4-hydroxy-3,4-dihydronaphthalen-1Â(2H)-one were also synthesized with excellent stereoselectivity
and high yields (71–89%) using the enzymatic cascades. The
investigation of NostocER–T4HNR-cascade reduction
of menadione, plumbagin, and 5-methoxymenadione revealed specificity
of tetrahydroxynaphthalene reductase toward these substrates. In addition,
the kinetic studies showed a high catalytic efficiency of NostocER
and T4HNR toward plumbagin and dihydroplumbagin, respectively,
compared to other enzymes