Analysis of racemic acid derivitives by chiral high performance liquid chromatography

Analysis of racemic acid derivitives by chiral high performance liquid chromatography Tara Kuknyo Orech, Knox College

Overview ,[object Object],[object Object],[object Object],[object Object]

What is HPLC? ,[object Object],[object Object],[object Object],[object Object],[object Object],Nelson, David L., Albert L. Lehninger, and Michael M. Cox. "3.3 Working with Proteins." Lehninger Principles of Biochemistry . New York: W.H. Freeman, 2008. Print. http://www.cnwtech.eu/HPLC-CNW.png http://www.onu.edu/files/images/chemistry/HPLC.jpg

Chirality ,[object Object],[object Object],[object Object],[object Object],http://www.answersingenesis.org/images/chirality-rgb.jpg

Chiral Chromatography ,[object Object],[object Object],[object Object],"Online Guide to Chiral HPLC." Mark Earll's Homepage . Web. 20 Aug. 2009. <http://www.raell.demon.co.uk/chem/CHIbook/chiral.htm>.

Column Used ,[object Object],[object Object],[object Object],[object Object],Chiral Selector: N(3,5-dinitrobenzoyl)-L-phenylglycine Nucleosil Silica "NUCLEOSIL CHIRAL." MACHEREY-NAGEL Homepage . 2011. Web. 13 Apr. 2011. <http://www.mn-net.com/tabid/6150/default.aspx>.

Disadvantages to Chiral HPLC ,[object Object],[object Object],[object Object],"Online Guide to Chiral HPLC." Mark Earll's Homepage . Web. 20 Aug. 2009. <http://www.raell.demon.co.uk/chem/CHIbook/chiral.htm>.

Why Chiral Chromatography? ,[object Object],[object Object],[object Object],[object Object]

What is a β-amino phosphonic acid? α β * * Abrams, Martha Leigh. “Progress towards the synthesis of phosphorus analogs of β -amino acids.” Knox College Honors Thesis, May 2008.

β-Amino Phosphonic Acids ,[object Object],[object Object],S-Phenylalanine S-Tyrosine S-Valine

FMOC-Derivative ,[object Object],[object Object],Kortenaar, Paul B.W. et al.""Rapid and Efficient Method for the Preparation of F-moc-amino Acids Starting from 9-fluorenylmethanol."" International Journal of Peptide and Protein Research 26.4 (1996): 398-400. Web. 12 Jan. 2009

Method ,[object Object],[object Object],[object Object]

Optimized Factors ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

Initial Readings Problem: both at 8 minutes! S-Valine R-Valine

Separation of the Peaks ,[object Object],[object Object],[object Object],[object Object],[object Object],L-Valine with x5 TFA

Extractions of FMOC-Cl Before extractions One extraction Two extractions

Re-Optimized! ,[object Object],[object Object],[object Object],[object Object],S-valine

Future Research ,[object Object],[object Object],[object Object]

Project 2: Racemic Dimethyl 1-hydroxybenzylphosphonate Pogatchnik, D. M., Weimer, David F. “Enantioselective Synthesis of α -Hydroxy Phosphonates via Oxidation with (Camphor Sulfonyl). University of Iowa Department of Chemistry . 1997.

Optimal Settings Flow Rate 1.0 mL/min Wavelength 285 nm Output Range 1.0 Amplifier Setting 0-200mV Sample Concentration 4 mmol Sample Size 5 μ L Solvent Heptane Dioxane TFA 100:20:.1 Eluent Heptane Dioxane TFA 100:20:.1

Results Total Average 69.14 : 30.86 +/- 1.39 Average of Batch 1 68.5 : 31.5 +/- 1.42 Average of Batch 2 69.95 : 30.05 +/- .94

Future Research ,[object Object],[object Object],[object Object],[object Object],[object Object],N(3,5-dinitrobenzoyl)-L-phenylglycine N(3,5-dinitrobenzoyl)-D-phenylglycine

Thank You! ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

Analysis of racemic acid derivitives by chiral high performance liquid chromatography

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Analysis of racemic acid derivitives by chiral high performance liquid chromatography