Which of the following dipeptides is formed when leucine is treated with (Boc)₂O and glycine is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?

Question

Quizplus · Accepted Answer

The first step in synthesizing the dipeptide from leucine and glycine is to protect the amino group of leucine with Boc. Then, glycine is protected with a benzyl group using benzyl alcohol/acid. The intermediate products are then combined using DCC as a coupling agent to form the dipeptide. Finally, the protecting groups are removed using trifluoroacetic acid and aqueous NaOH to yield the dipeptide. Based on this synthesis, the only possible dipeptide that can be formed is Leu-Gly.

Which of the Following Dipeptides Is Formed When Leucine Is