We report the synthesis of β,β‐dinaphthyl amino acids by directed CH‐activation and their subsequent utilization in peptides. The synthesis of aromatic β‐branched amino acids is limited by sterical crowding for large aromatic ring systems. The amino acids are transformed into adequately protected building blocks for solid phase peptide synthesis by using our amide weakening strategy. Our aim was to study the interactions of the side chain aryl groups in solution and solid state. Based on quantitative analysis of 1H NMR reference nuclei, we investigate conformational equilibria and compare them to established gearing systems.

中文翻译：

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β，β-二栉酰氨基酸的合成：走向肽和微型蛋白的分子齿轮


我们报道了通过定向 CH 激活合成 β，β-二萘基氨基酸及其随后在肽中的利用。芳香族β支链氨基酸的合成受到大型芳香族环系统的空间拥挤的限制。通过使用我们的酰胺弱化策略，氨基酸被转化为充分保护的构建单元，用于固相肽合成。我们的目的是研究侧链芳基在溶液和固态下的相互作用。基于对 1H NMR 参考核的定量分析，我们研究了构象平衡并将其与已建立的齿轮系统进行比较。