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首页> 外文期刊>Chemistry: A European journal >Epimerization-Free C-Terminal Peptide Activation
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Epimerization-Free C-Terminal Peptide Activation

机译：无差向异构C末端肽激活

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摘要

Peptides constitute a very important compound class in drug research. Thus, racemization-free peptide synthesis is of key importance to acquire the required peptide chains in diastereomerically pure form. In general, the way to synthesize peptides with full stereointegrity is by elongation at the N terminus. On the other hand, methods that allow epi- merization-free C-terminal peptide activation would greatly enhance the available routes and would be a highly valuable synthetic tool for obtaining the desired peptides. Especially for the convergent solution-phase synthesis of peptides by segment coupling a reliable and epimerization-free C-terminal activation methodology is required. Recently, Danishefsky showed the utility of peptide 4-nitrophenyl esters in peptide segment couplings. These esters were prepared by EDCl/HOBt-mediated coupling of the amino acid 4-nitrophenylesters to the C terminus of peptides. Due to otherwise inevitable epimerization this methodology is restricted by the requirement of a glycine residue at the C-terminal penultimate position. Herein, we disclose our initial results on the development of a racemization-free C-terminal peptide activation through the copper(II)-mediated Chan–Lamtype coupling between peptides and arylboroxines and subsequent amine-coupling reactions (Scheme 1).
机译：肽构成药物研究中非常重要的化合物类别。因此，无外消旋的肽合成对于获得非对映体纯形式的所需肽链至关重要。通常，合成具有完全立体完整性的肽的方法是通过在N末端延伸。另一方面，允许无差向异构C末端肽活化的方法将大大增强可用途径，并且将成为获得所需肽的极有价值的合成工具。特别是对于通过片段偶联的肽的收敛性溶液相合成，需要可靠且无差向异构的C末端活化方法。最近，Danishefsky显​​示了肽4-硝基苯基酯在肽片段偶联中的用途。这些酯是通过EDC1 / HOBt介导的氨基酸4-硝基苯基酯与肽的C末端偶联而制备的。由于否则不可避免的差向异构化，因此该方法受到C末端倒数第二个位置的甘氨酸残基的要求的限制。在这里，我们通过肽和芳基硼氧烷之间的铜（II）介导的Chan-Lamtype偶联以及随后的胺偶联反应，公开了无消旋C末端肽活化的初步结果（方案1）。

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