Enantioselective Biotransformation of Prochiral Ketone via Daucus carota
Ryan Smith, Charlie Knox, and Elizabeth Davis
Faculty Advisor: Dr. Michele Harris
Department of Chemistry
Stephen F. Austin State University
Reaction
5µl SN 50%
5µl RS 50%
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 Incubated carrots with ketone, extracted
alcohol product, measured optical activity,
and verified product using IR spectroscopy.
 Incubated carrot strips in buffer with low
percent detergent . Used ammonium sulfate
precipitation. Analyzed both supernatant
and pellet using SDS-PAGE.
 Placed known quantity of purified alcohol on
disk and placed on a Petri dish growing
bacteria.
10 µl SN
SDS-PAGE Results
10 µl RS
Biotransformations of prochiral ketones can be
performed using plant cells. The benefits of
using
plant
cells
include
low
cost,
environmentally sound procedures compared to
conventional chemical processes, and the
stereospecific
nature
of
the
reaction.1,2
Benzofuran-2-yl methyl ketone was reduced to ()-benzofuran-2-yl-ethanol after incubation with
carrots
in
water.
The
reaction
was
enantioselective in that it produced the S-isomer
as indicated by optical activity. Currently,
attempts to isolate the carrot enzyme and
antimicrobial studies of the (-)-benzofuran-2-ylethanol product are underway.
Methods
STD
Abstract
Optical Activity Results
 The optical activity of the alcohol product
agreed with literature values of -16.4 and the
percent yield was 37%.
IR Spectroscopy Results
Arrows indicate protein bands
isolated from carrot surface.
Antibacterial Results
Possible Reaction Pathway
Ring of inhibition of
bacterial growth. The
concentration of the
alcohol was 1.5
mg/ml.
Ketone
105
100
95
90
85
References
1. Ravia, S. et.al. J.Chem.. 2006, 83, 1049-1051
2. Yadav, J.S.; et.al. J. Org. Chem., 2002, 67, 3900-3903
3. Yang, Z.; et.al. J. Micro. Biotech., 2008, 35, 1047-1051
Alcohol
803.44
941.46
1005.68
739.60
35
Conclusions
878.92
40
1453.85
45
1253.29
50
1073.48
1172.12
55
1022.22
3349.33
60
1152.80
70
65
Funding for this project was provided by the Robert A.
Welch Departmental Grant (AN-0008) and from SFASU
Office of Research and Sponsored Programs Faculty
Research Grant
1300.84
75
%T
Funding
80
30
4000
3500
3000
2500
2000
1500
1000
500
Wavenumbers (cm-1)
Acknowledgements
The following students collaborated on this project:
Betty Abraha, Adrianne Crandall, Natasha Impink
Hernandez, Olivia Korpe, John Sharp, and Kenneth
Smith.
This undergraduate group effort has
worked out the preliminaries for:
 isolating pure, optically active alcohol
 demonstrated carrot protein can be
removed from surface of carrot, and
 the alcohol may some antibacterial
properties at fairly high concentrations.