Solution Found!
When the N terminus of a peptide is acetylated, the
Chapter 25, Problem 25.75(choose chapter or problem)
When the N terminus of a peptide is acetylated, the peptide derivative that is formed is unreactive toward phenyl isothiocyanate. Explain. N H H PEPTIDE Acetylation N H PEPTIDE O
Questions & Answers
QUESTION:
When the N terminus of a peptide is acetylated, the peptide derivative that is formed is unreactive toward phenyl isothiocyanate. Explain. N H H PEPTIDE Acetylation N H PEPTIDE O
ANSWER:Step 1 of 2
In this exercise, we’re told that when the N-terminus of a peptide is acetylated, the peptide derivative that is formed is unreactive towards phenyl isothiocyanate. We’re asked to explain this phenomenon.
Recall that phenyl isothiocyanate is a common reagent in peptide chemistry, as it’s used in Edman degradations in order to sequence a peptide chain. The isothiocyanate group is very electrophilic, and can be attacked by a good nucleophile such as the amino group of a peptide to form a PTH derivative. That’s the whole basis of an Edman degradation.