The herbicide glyphosate (Roundup®) kills plants by inhibiting an enzyme needed for synthesis of phenylalanine. Deprived of phenylalanine, the plant cannot make the proteins it needs, and it gradually weakens and dies. Although a small amount of glyphosate is deadly to a plant, its human toxicity is quite low. Suggest why this powerful herbicide has little effect on humans.

Most naturally occurring amino acids have chiral centers (the asymmetric α carbon atoms) that are named (S) by the Cahn–Ingold–Prelog convention (Section 5-3). The common naturally occurring form of cysteine has a chiral center that is named (R), however.

(a) What is the relationship between (R)-cysteine and (S)-alanine? Do they have the opposite three-dimensional configuration (as the names might suggest) or the same configuration?

Draw the structure of the predominant form of

(d) glutamic acid at pH 7.

Draw three-dimensional representations of the following amino acids.

(d) L-tryptophan

Draw the structure of the predominant form of

(b) proline at pH 2.

Most naturally occurring amino acids have chiral centers (the asymmetric α carbon atoms) that are named (S) by the Cahn–Ingold–Prelog convention (Section 5-3). The common naturally occurring form of cysteine has a chiral center that is named (R), however.

(b) (S)-Alanine is an L-amino acid (Figure 24-2). Is (R)-cysteine a d-amino acid or an L-amino acid?

Draw the structure of the predominant form of

(a) isoleucine at pH 11.