N-Boc-N-(2-(tritylthio)ethoxy)glycine has been developed as a building block for peptide ubiquitination, which is fully compatible with solid-phase Fmoc chemistry and common peptide modifications including phosphorylation, methylation, acetylation, biotinylation, and fluorescence labeling. The optimal conditions for peptide cleavage and auxiliary removal were obtained. The utility of this building block in peptide ubiquitination was demonstrated by the synthesis of seven ubiquitinated histone and Tau peptides bearing various modifications. Cys residues were well tolerated and did not require orthogonal protection. The structural integrity and folding of the synthesized ubiquitinated peptides were confirmed by enzymatic deubiquitination of a fluorescently labeled ubiquitin conjugate. The synthetic strategy using this building block provides a practical approach for the preparation of ubiquitinated peptides with diverse modifications.

中文翻译：

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N-叔丁氧基羰基-N-(2-(三苯甲基硫基)乙氧基)甘氨酸作为肽泛素化的构建模块

N -Boc- N -(2-(三苯甲基硫基)乙氧基)甘氨酸已被开发为肽泛素化的构建模块，它与固相 Fmoc 化学和常见的肽修饰完全兼容，包括磷酸化、甲基化、乙酰化、生物素化和荧光标记。获得了肽裂解和辅助去除的最佳条件。通过合成七种带有各种修饰的泛素化组蛋白和 Tau 肽，证明了该构建模块在肽泛素化中的实用性。Cys 残基耐受性良好，不需要正交保护。通过荧光标记的泛素缀合物的酶促去泛素化证实了合成的泛素化肽的结构完整性和折叠。使用该构建模块的合成策略为制备具有多种修饰的泛素化肽提供了一种实用方法。