Asymmetric hydrogenation of the C–C double bond of 1- and 1,2-methylated maleimides with cultured suspension cells of Marchantia polymorpha

Abstract

Suspension cultured cells of Marchantia polymorpha have a potentiality to hydrogenate the CC double bonds of 2-methyl-and 2,3-dimethylmaleimide derivatives to give optically pure (2R)-2-methyl-and (2R,3R)-2,3-dimethylsuccinimide derivatives, respectively.

Highly enantioselective reduction of the C–C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl- maleimides by fungal strains

“…Our results with the filamentous fungi of the genera Aspergillus, Fusarium, and Penicillium are similar to those obtained by Hirata et al [7][8][9] with a cultured suspension of plant cells. They have recently demonstrated that Nicotiana tabacum, Catharanthus roseus, Parthenocissus tricuspidata, and Cynechococcus sp.…”

“…Some of these structures have been demonstrated to be good substrates for biocatalysis with cultured plants cells. [7][8][9] 2. Results and discussion N-Phenyl maleimides 1-2 obtained through reported procedures 10,11 (125 mg each) in DMSO (5 mL) were poured into flasks containing the fungal biomass in 250 mL of culture media.…”

Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase

“…For example, the enantiopure succinimides 4b are building blocks for the synthesis of biologically active natural products, such as, pyrrolizidine and indolizidine alkaloids (Hegazy et al 2006). Although it has been achieved using other enoate reductases (Hegazy et al 2006;Sortino and Alicia Zacchino 2010;Sortino et al 2009), the reported substrate concentration only reached 5 mM (0.94 g/l). On the contrary, the present system can well tolerate a substrate concentration of 54 mM (10 g/l).…”

Two “classical” Old Yellow Enzymes from Chryseobacterium sp. CA49: Broad substrate specificity of Chr-OYE1 and limited activity of Chr-OYE2

“…Substrates 12a and 13a were also efficiently reduced with excellent stereoselectivity (>99% ee) ( Table 3). The activity of Chr-OYE1 toward 12a was comparable with other ene-reductases, and the stereoselectivity was the same as NCR-reductase, OYE 1-3 and Achr-OYE4 to yield the (R)-product [20,26,34,36], which is a building block for the synthesis of biologically active natural products, such as pyrrolizidine and indolizidine alkaloids [37]. For substrate 13a, OYE1-3 and NCR-reductase have been reported to show complementary stereoselectivity, yielding the (R)-and (S)-13b with 68-90% ee and >99% ee, respectively [34].…”