Daucus carota and baker’s yeast mediated bio-reduction of prochiral ketones

Stereoselective reduction of prochiral ketones to the corresponding alcohols using biocatalysts has attracted much attention, from the viewpoint of green chemistry. Asymmetric reduction of indanone, tetralone and hydroxyl trimonoterpene ketones to the corresponding enantiomerically pure (S)-alcohols, using Daucus carota plant homogenate and fermented baker’s yeast cells, is described. The present study illustrates the broad substrate selectivity of the dehydrogenase enzymes present in the D. carota in the synthesis of a wide range of chiral secondary alcohols of biological importance.

Graphical abstractStereo selective bio-reduction of prochiral ketones like, indanones, tetralones and mono terpene ketones into chiral secondary alcohols using Daucus carota root homogenate and fermented baker’s yeast cells is described. The application of this methodology in asymmetric bio-reduction of ketones has shown wide substrate specificity, good yields and enantioselectivity in mild and eco-friendly environment.Figure optionsDownload full-size imageDownload as PowerPoint slide

(R)-2-Hydroxy-1-indanone-oximeC9H9NO2Ee = 80% (D. carota)[α]D25=+48.2 (c 0.8, MeOH)Absolute configuration: (R)

7-Methyl-(R)-2-hydroxy-1-indanone-oximeC10H11NO2Ee = 88% (D. carota)[α]D25=+58.5 (c 0.7, MeOH)Absolute configuration: (R)

4-Methyl-(R)-2-hydroxy-1-indanone-oximeC10H11NO2Ee = 85% (D. carota)[α]D25=+78.5 (c 0.9, MeOH)Absolute configuration: (R)

7-Isopropyl-(R)-2-hydroxy-1-indanone-oximeC12H15NO2Ee = 88% (D. carota)[α]D25=+23.5 (c 1.0, MeOH)Absolute configuration: (R)

5-Bromo-(R)-2-hydroxy-1-indanone-oximeC9H8BrNO2Ee = 80% (D. carota)[α]D25=+39.5 (c 0.6, MeOH)Absolute configuration: (R)

5,6-Bromo-(R)-2-hydroxy-1-indanone-oximeC9H7Br2NO2Ee = 80% (D. carota)[α]D25=+52.5 (c 0.9, MeOH)Absolute configuration: (R)

cis-(1R,2S)-1-Amino-2-indanolC9H11NOEe = 99% (D. carota)[α]D25=+56.6 (c 0.8, MeOH)Absolute configuration: (S)

7-Methyl-cis-(1R,2S)-1-amino-2-indanolC10H13NOEe = 98% (D. carota)[α]D25=-112.2 (c 0.6, CHCl3)Absolute configuration: (S)

4-Methyl-cis-(1R,2S)-1-amino-2-indanolC10H13NOEe = 95% (D. carota)[α]D25=-29.6 (c 0.6, CHCl3)Absolute configuration: (S)

7-Isopropyl-cis-(1R,2S)-1-amino-2-indanolC12H17NOEe = 90% (D. carota)[α]D25=-113.1 (c 0.5, CHCl3)Absolute configuration: (1R,2S)

5-Bromo-cis-(1R,2S)-1-amino-2-indanolC9H10BrNOEe = 95% (D. carota)[α]D25=-32.1 (c 0.8, MeOH)Absolute configuration: (1R,2S)

5,6-Bromo-cis-(1R,2S)-1-amino-2-indanolC9H9Br2NOEe = 96% (D. carota)[α]D25=-33.5 (c 1.5, CHCl3)Absolute configuration: (1R,2S)

2-TetralolC10H12OEe = 85% (D. carota)[α]D25=-19.2 (c 0.9, CHCl3)Absolute configuration: (S)

7-Methoxy-2-tetralolC11H14O2Ee = 70% (D. carota)[α]D25=+16.1 (c 1.0, CHCl3)Absolute configuration: (S)

7,8-Dimethoxy-2-tetralolC12H16O3Ee = 80% (D. carota)[α]D25=+19.1 (c 0.43, CHCl3)Absolute configuration: (S)

NeomentholC10H20OEe = 99% (D. carota)[α]D25=-21.2 (c 0.21, CHCl3)

NeoisodihydrocarveolC10H18OEe = 95% (D. carota)[α]D25=-18.08 (c 0.71, CHCl3)

IsopulegolC10H18OEe = 90% (D. carota)[α]D25=-22.1 (c 0.91, CHCl3)