An octapeptide was completely hydrolyzed to yield the follow…
An octapeptide was completely hydrolyzed to yield the following set of eight amino acids (listed in alphabetical order; this is not the sequence): 2 Ala, 2 Lys, Met, Val, 2 Tyr (AAKKMVYY). Unfortunately, your lab is poor and you cannot afford an amino acid sequencer. However, you are capable of doing “old-school” chemistry and you obtain the following information: 1) Treatment of the octapeptide with cyanogen bromide did not cleave the octapeptide. 2) The octapeptide was treated with Sanger’s reagent and then completely hydrolyzed. One of the residues isolated was DNP-Val. 3) Treatment of the octapeptide with chymotrypsin yielded tyrosine, a tripeptide, and a tetrapeptide. The three fragments were separated via chromatography and the tripeptide was then treated with Sanger’s reagent and hydrolyzed. One of the three residues isolated from the hydrolyzed tripeptide was DNP-Val. 4) Treatment of the octapeptide with trypsin yielded lysine, a dipeptide, and a pentapeptide. The three fragments were separated via chromatography and the pentapeptide was then treated with Sanger’s reagent and hydrolyzed. One of the five residues isolated from the hydrolyzed pentapeptide hydrolysis was DNP-Val. What is the sequence of the original octapeptide?