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The concept of topographic design of peptide neurotransmitters and hormones was pioneered by Hruby (
1
,
2
). When the design involved primarily constraint of the side chains of a peptide that has a well-defined backbone conformation, the term “topographic design on a stable template” was proposed (
3
). The side chain χ
1
of aromatic amino acids, such as Phe, Trp, Tyr, and His, can be constrained in either the gauche (−) or gauche (+) conformation by linking the nitrogen atom to the aromatic ring through a methylene bridge (Fig. 1 ).Fig. 1.
Principle of side-chain constraint for Phe, Trp, and His.
