a) Detail how you would use the amidomalonate synthesis to prepare a racemic mixture of leucine. Include in your answer

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A Detail How You Would Use The Amidomalonate Synthesis To Prepare A Racemic Mixture Of Leucine Include In Your Answer 1 (66.14 KiB) Viewed 25 times

a) Detail how you would use the amidomalonate synthesis to prepare a racemic mixture of leucine. Include in your answer a mechanism for the reaction. [6 marks) b) Consider the following experimental results: Total hydrolysis of a nonapeptide gave: Ala, Arg, Glu, Leu, Lys, Met,Phe,Tyr, Val • One fragment from CNBr treatment was: Tyr-Leu-Lys • One fragment from Chymotrypsin treatment was Arg-Glu-Met-Tyr One fragment from Trypsin treatment was Val-Ala-Phe-Arg i. Deduce, with suitable explanations, the amino acid sequence of the nonapeptide. ii. The reagent shown below is widely utilized in the sequencing of peptides. Treatment of the nonapeptide you deduced in part i. with this reagent yields a phenylthiohydantoin derivative, compound 1, and an octapeptide. Write a mechanism for the formation of compound 1. N=C=S [9 marks) c) The Merrifield solid phase synthesis is commercially used for the production of peptides. Identify all of the steps necessary to prepare the peptide Ala-Val-Leu-Ile with a Merrifield synthesis using DCC, Fmoc and any other readily available reagents. In your answer, include the coupling mechanism and protection mechanism (ONLY ONCE). [10 marks