In the olden days (the \(1970 \mathrm{~s})\), the sequence of amino acids in a
protein was determined by running a series of chemical reactions known as the
Edman degradation. This technique worked only on short peptide chains,
however, and large proteins had to be broken down into small parts in order to
be sequenced. One way to chop large proteins into small chains was with
enzymes known as proteases. The protease trypsin breaks the amide bond on the
\(\mathrm{CO}_{2} \mathrm{H}\) side of arginine and lysine, and the protease
chymotrypsin breaks the amide bond on the \(\mathrm{CO}_{2} \mathrm{H}\) side of
tyrosine, phenylalanine, and tryptophan. An octapeptide treated with trypsin
breaks down to the peptides Ala-Gly-Trp-Gly-Lys and Thr-Val-Lys, and the same
octapeptide treated with chymotrypsin breaks down to the peptides Gly-Lys and
Thr-Val-Lys-Ala-Gly-Trp. What is the sequence of the octapeptide?