The synthesis and stability of allyloxycarbonyl (Aloc) indole-protected Trp derivatives and their application in solid-phase peptide synthesis are reported. The study shows that the Aloc protection on the indole moiety is suitable for orthogonal protection in the Fmoc/tBu strategy if the Fmoc group is cleaved with DBU. Several tryptophan-containing peptides have been synthesized including dynorphin A-(1-13), which has been intensively studied with respect to side reactions during the final TFA cleavage procedure. The results demonstrate the protective function of the Aloc group on the Trp during final deprotection. Furthermore, it could be demonstrated that Trp(Aloc)-containing peptides can be isolated and that the Aloc group can then be removed in a second step. The synthesis of phosphorylated delta sleep inducing peptide (P-DSIP) using the global phosphorylation approach provides another example in which Trp indole protection by Aloc prevents the formation of oxidative side products.

中文翻译：

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烯丙氧基羰基保护基在Trp吲哚在固相肽合成中的应用*

报道了烯丙氧基羰基（Aloc）吲哚保护的Trp衍生物的合成和稳定性及其在固相肽合成中的应用。研究表明，如果Fmoc基团被DBU裂解，则吲哚部分的Aloc保护适合于Fmoc / tBu策略中的正交保护。已经合成了几种包含色氨酸的肽，包括强啡肽A-（1-13），已对其在最终TFA裂解过程中的副反应进行了深入研究。结果证明了最终脱保护过程中Aloc基团对Trp的保护作用。此外，可以证明可以分离出含有Trp（Aloc）的肽，然后可以在第二步中除去Aloc基团。