Stereoselective Oxidation of 1‐Phenyl‐1,2‐propanediol Mediated by Microorganisms

Abstract

The enantioselective oxidation of (1R,2S)‐1‐phenyl‐1,2‐propanediol [(1R,2S)‐1], mediated by baker’s yeast, gave (−)‐(S)‐1‐phenyl‐2‐hydroxy‐1‐propanone [(S)‐2] in 64 % isolated yield and 93 % ee. Kinetic experiments of the bio‐oxidation of (±)‐anti‐1 revealed that the enantiomer (1R,2S)‐1 was more reactive than (1S,2R)‐1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1S,2R)‐1 in >99 % ee from (±)‐anti‐1. The preparation of (1S,2R)‐1 is interesting, as it is the antipode of the product obtained by the reduction of 1‐phenyl‐1,2‐propanedione using baker’s yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (±)‐anti‐1. The best result was obtained using Geotrichum candidum, which gave (1S,2R)‐1 in 32 % yield and 99 % ee.

Regio- and enantio-selective oxidation of diols by Candida parapsilosis ATCC 7330

“…50 Signicantly, the current study presents a simple method for the preparation of optically pure diols with good ee and yields, together with the corresponding keto alcohols under mild reaction conditions at room temperature. 32 In the present method, (S)-2-hydroxy-1-phenylpropan-1-one 7a was Introduction of a double bond between the phenyl ring and diol in the case of 9 (Chart 1, Oxidation of 9 to 9a has not been reported so far in the literature. To expand the substrate scope, different substrates, in particular 7-11 (Chart 1, Table 3 Here the increase in erythro and decrease in threo in the case of 7b compared to the starting diol 7 indicates that one of the threo forms is oxidised.…”

“…23 Candida parapsilosis ATCC 7330 has been used for deracemization of sec alcohols, asymmetric reduction of prochiral ketones and separation of DL-N-protected amino acid esters. 32 Similarly, asymmetric oxidation of (1S,2S)-1,2-diphenylethane-1,2-diol was reported using N-bromosuccinimide in the presence of a chiral copper catalyst. 29 Another mechanistic investigation of such deracemization using a deuterated substrate also showed the formation of an undeuterated product, which is possible when the oxidation of an enantiomer is followed by its reduction.…”

Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures

“…The selected microorganism comprised: yeast of the genus Rhodotorula: R. rubra KCh 4, R. rubra KCh 82, and R. glutinis KCh 242; of the genus Candida: C. wiswanathi KCh 120, C. parapsilosis KCh 909, C. sake KCh 908, and C. pelliculosa ZP22; of the genus Saccharomyces: S. cerevisiae KCh 464, S. brasiliensis KCh 905, and S. pastorianus KCh 906 and two other yeast strains: Y. lipolytica KCh 71 and Z. bailii KCh 907. The biocatalysts were selected based on their biocatalytic properties, such as fast growth rate, capability for effective enantioselective reduction of aliphaticaromatic ketones and oxidation of the respective alcohols [30][31][32][33]. Moreover, unlike in the case of filamentous fungi, in the cultures of yeasts competitive reactions such as hydroxylation, dehydratation and degradation rarely occur [34,35].…”

Whole‐Cell Biocatalysis in Seawater: New Halotolerant Yeast Strains for the Regio‐ and Stereoselectivity Reduction of 1‐Phenylpropane‐1,2‐Dione in Saline‐Rich Media

“…Other more recently described biocatalytic routes to chiral acyloins are, among many others, the enantioselective α‐hydroxylation of ketones catalyzed by cytochrome P450 monooxygenases (CYPs) or the stereoselective oxidation of 1,2‐diols mediated by different microorganisms …”