Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst

Abstract

The increasing demand for biocatalysts in synthesizing enantiomerically pure chiral alcohols results from the outstanding characteristics of biocatalysts in reaction, economic, and ecological issues. Herein, fifteen yeast strains belonging to three food originated yeast species Candida zeylanoides, Pichia fermentans, and Saccharomyces uvarum were tested for their capability for asymmetric reduction of acetophenone to 1-phenylethanol as biocatalysts. Of these strains, C. zeylanoides P1 showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high yields. The preparative scale asymmetric bioreduction of 4-nitroacetophenone (1m) by C. zeylanoides P1 gave (S)-1-(4-nitrophenyl)ethanol (2m) with 89% yield and > 99% enantiomeric excess. Compound 2m has been obtained in an enantiomerically pure and inexpensive form. Additionally, these results indicate that C. zeylanoides P1 is a promising biocatalyst for the synthesis of chiral alcohols in industry.

Revisitation of the Preparation of (S,S)‐2,8‐Diazabicyclo[4.3.0]nonane Through Enzymatic Resolution.

“…Enzymes play a crucial role in green chemistry as they function as catalysts, accelerating chemical reactions without requiring harsh reaction conditions or chemicals, and are also reusable. [6][7][8][9][10][11][12][13][14] A chemo-enzymatic strategy via kinetic resolution of cis-(�)-dimethyl 1-acetylpiperidine-2,3-dicarboxylate (cis-13) has been claimed in a patent by FIS Italian Factory Synthetic SPA (Scheme 4). [15] It involves the use of covalently immobilized lipase B from Candida antarctica (CAL B).…”

Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

“…In addition, chiral secondary alcohols can be synthesized by isolated enzyme, but expensive reducing co‐enzymes, such as NADPH, and purification of enzymes are indispensable for this reaction. These disadvantages limit its use in industrial‐scale production. When compared with isolated enzymes, whole‐cell application is mostly preferred due to its cheap and effective application process as no cofactors are required as they are present in the cytoplasm unlike the purified enzymes, which require them.…”

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

“…Chiral reduction is limited because of the enantioselectivity, cost of the chiral reductants and environmental issues although it is widely used in commercial production (Hodgkinson et al ., 2014). Biocatalytic reduction seems to be the most potential and competitive industrialization process compared with chemical catalysis due to its clean and ecofriendly way, mild reaction conditions and high selectivity for the substrate, which is reflected in the application of some important products (Şahin and Dertli, 2017). It is reported that the chiral compounds produced by biocatalytic reduction accounted for 20% of the total chiral alcoholic intermediates in industrial products (Honda et al ., 2017).…”