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Download AMINO ACIDS Ethan Secor, John N. Gitua (Mentor)
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Transcript
METALLORGANIC SYNTHESIS OF -AMINO ACIDS Ethan Secor, John N. Gitua (Mentor) Department of Chemistry, College of Arts and Sciences Drake University RESULTS Amino acids are important biological compounds and are widely used in chemical synthesis. They are characterized by a carboxylic acid group and an amine group. When these groups are attached to the same carbon atom the compound is known as an -amino acid. Here we present a mechanism for synthesis based on the metallorganic reaction of imines. SUMMARY PROPOSED REACTION MECHANISM Infrared spectra suggest the presence of a carboxylic acid functional group The reaction and products are sensitive to conditions such as exposure to air and heat. % Transmittance INTRODUCTION The proposed reaction for a-amino acid synthesis uses a metallorganic mechanism. A titanium complex coordinates to the C=N double bond, and carbon dioxide inserts into this metallocycle. Upon hydrolysis, the ring is cleaved and the product is formed. The product was isolated using a series of extractions and characterized by infrared spectroscopy. 1) Ti complex, BuLI -78⁰C, THF 2) Carbon Dioxide RT 3) Hydrochloric Acid RT Wavenumber (cm-1) CONCLUSIONS The infrared spectra suggest there may be amino acid formation The results are not conclusive • UV-Vis should be done and compared to a standard • NMR data would help ascertain identity • RPLC would help ascertain purity EXPERIMENTAL PROCEDURE The titanium complex was prepared in purified tetrahydrofuran using titanium(IV) isopropoxide and butyl lithium at low temperatures maintained by mixing acetone and dry ice. The imine was added to this mixture. The reaction mixture was gradually warmed to room temperature. Carbon dioxide was introduced from the sublimation of dry ice. Finally, hydrochloric acid was added to quench the reaction. The organic layer was extracted, and the aqueous layer was neutralized with sodium hydroxide. Diethyl ether was added to the aqueous layer and extracted. The two organic extractions were dried and characterized by infrared spectroscopy. FUTURE WORK Further work will be performed using different imines for the preparation of -amino acids and other classes of amino acids. Other analytical techniques, such as NMR, will by used to characterize reaction products. REFERENCES Spectral Database for Organic Compounds, SDBS. AIST. SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology)