Dipeptide synthesis - Synthesis of a Protected Dipeptide...

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Synthesis of a Protected Dipeptide David Grauer Jimin Kim Tuesday Lab Section
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Purpose This lab sought to synthesize a dipeptide using two protected peptides to form a protected dipeptide. Melting point and NMR analysis were used to discern which amino acids were used in the synthesis. Procedure The lab employed two protecting groups, methoxy and Boc to control the nucleophicity of the oxygen and nitrogen, respectively. DCC was used to help the dehydration reaction proceed. The dipeptide was then isolated through several extractions and rotary evaporation. The product was analyzed with NMR and melting points. Data and Observations Isolation of Boc-A: solid, white crystals. MP (A) = 81-82ºC (Benz. Acid = 120-122ºC). Mass = 371 mg Isolation of B – Me HCl: solid, white crystals. MP (B) = 159-160.5 ºC Mass = 688 mg Isolation of DCU: Mass = 412 mg
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Lab Questions 1. Please refer to the diagrams below for spectral assignments. The only splitting in this molecule occurs between Hyrdogens A and B. This splitting in H A , a doublet, corresponds to having one alpha Hydrogen on the adjacent Nitrogen.
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