Chemistry 30A3 Fall 2011 Labs Dr. Troendle 46

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 46 - 2 Give...

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Chemical Biology 3OA3, September 2009 Page 46 combined products. To do this, dissolve the sample in 1 mL of deuterated TFA (TFA-d), and transfer to an nmr tube. Take the sample to the TA in charge of the nmr spectrometer, and obtain the spectrum. Share this spectrum amongst the students who generated the sample, and interpret the spectrum in your report. [NOTE: the product peptides are not stable in TFA overnight; if you do this, you need to record the spectrum within an hour or two]. 4. Q UESTIONS : 1. Proton nmr data and a COSY spectrum for a peptide are given in the Appendix. Interpret this data to assign resonances as far as is possible.
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Unformatted text preview: 2. Give mechanisms for each of the chemical steps involved in the synthesis of your peptide. Where needed, some helpful hints are provided in the Scheme in the introduction. 3. Use the appropriate mechanism above to explain why the Rink resin gives a peptide amide, rather than a peptide. What feature(s) of the resin would you modify to turn it into a resin that could be used to make regular peptides? 5. R EFERENCES : This laboratory was adapted from Truran, G.A.; Aiken, K.S.; Fleming, T.R.; Webb, P.J; Hodge Markgraf, J., J. Chem. Educ. , 79 , 85 (2002)....
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