Facile biocatalytic reduction of the carbon–carbon double bond of 5-benzylidenethiazolidine-2,4-diones. Synthesis of (±)-5-(4-{2-[methyl(2-pyridyl)amino]ethoxy}benzyl)thiazolidine-2,4-dione (BRL 49653), its (R)-(+)-enantiomer and analogues

Yeast cell factories for fine chemical and API production

“…However, also alternative yeasts were described to be active. Geotrichum candidum [ 77 ], Rhodotorula rubra [ 78 ] and Rhodosporidium sp. [ 78 ] were found to possess enoate reductases, active for diverse non-natural α,β-unsaturated carbonyl- and carboxyl-compounds, respectively [ 71 ].…”

Reductive Aldol‐type Reactions in the Synthesis of Pharmaceuticals

“…Therefore, Cantello and co-workers investigated the possibility for biocatalytic reduction of the intermediate 2.4.b. [60] The best results were demonstrated by Immobilised Rhodotorula rubra CBS 6469 (the yeast species) at 28 °C in 22 h. Yet, the yield of the target molecule was less than 52 % (Scheme 12(c)).…”

Biocatalyzed synthesis of antidiabetic drugs: A review

“…Thus, it is possible to find in literature some examples of the resolution of both enantiomer of glitazones, either through their derivatization to diastereoisomers (Sohda et al 1984;Gahafu et al 2010;van Niel et al 2011avan Niel et al , 2011b or by preparative chiral HPLC (Calixto and Bonato 2013). On the other hand, the first example of stereoselective biocatalytic synthesis was described by researchers at SmithKline Beecham by means of the bioreduction of the precursor benzylidine compound 4 ( Figure 6), catalyzed by whole cells from red yeast Rhodotorula rubra CBS 6469 (Cantello et al 1994).…”

“…Over a 4 h reaction at pH 3.75, the product was found to be of >98% enantiomeric purity. These authors also described the use of alginate-entrapped immobilized cells for performing the bioreduction (Cantello et al 1994), which was further scaled-up by some other scientists of the same company (Heath et al 1997).…”