One-pot synthesis of (R)-1-(1-naphthyl)ethanol by stereoinversion using Candida parapsilosis

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

“…This highly enantioselective oxidation allowed us to obtain (2R,4R)-cis-flavan-4-ol (5) with the enantiomeric excess of over 97%. The capability of the C. parapsilosis strains for enantioselective oxidation of S-alcohols was reported earlier for racemic 1-arylethanols and allylic alcohols, which were deracemised to the (R)-enantiomer (ee up to >99%) by whole cells of C. parapsilosis ATCC 7330 culture [36][37][38].trans-Flavan-4-ol (7) underwent oxidation at much lower rate compared to the cis-alcohol in the cultures of almost all tested biocatalysts. In Table 3 we presented the results for five strains that were able to transform trans-flavan-4-ol (7).…”

“…The same selectivity was observed in deracemization of 1-aryl ethanol in the cultures of C. parapsilosis ATCC 7330 [36], Candida albicans CCT 0776 [37] and some bacterial strains [39,40], which proceeded via enantioselective oxidation of the (S)-enantiomer. In our previous research concerning bioreduction of propiophenone we observed that during incubation of propiophenone in the cultures of all tested microorganisms, longer biotransformation time resulted in a drop in a percent content of the S-alcohol, along with an increase in a percent content of the R-alcohol.…”

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

“…Instead of using isolated enzymes, a number of microbial stereoinversion systems as well as hybrid systems containing whole cells/isolated enzymes have also been reported in deracemisation via stereoinversion. [73][74][75][76][77][78][79][80][81] Here, it should, however, be mentioned that due to the presence of various endogenous ADHs and alcohol oxidases (AOxs) in the microbial "black-box" systems, the real deracemisation pathway may differ case by case from the depiction of Scheme 13; consequently, identifying suitable enantiocomplementary systems can be challenging. Scheme 14 depicts a selection of enantiomerically pure alcohols obtained through enzymatic and microbial deracemisation via stereoinversion.…”

Why Leave a Job Half Done? Recent Progress in Enzymatic Deracemizations

“…[95] It is important to highlight that in general long reaction times are required for the deracemization of secondary alcohols when using whole cells, therefore many investigations have been focused on overcoming this limitation. Recently, Chadha and co-workers have reported whole cell-mediated deracemizations of this type of substrates employing C. parapsilosis ATCC 7330 in phosphate buffer at 25 ºC.…”