Introducing Chemoselective Peptide Conjugation via N-Alkylation of Pyridyl-alanine: Solution and Solid Phase Applications,Organic Letters

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Introducing Chemoselective Peptide Conjugation via N-Alkylation of Pyridyl-alanine: Solution and Solid Phase Applications
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-13 , DOI: 10.1021/acs.orglett.4c03168
Soumit Dutta ₁ , Arnab Chowdhury ₁ , Anupam Bandyopadhyay ₁

Affiliation

A novel chemoselective peptide conjugation via late-stage N-alkylation of pyridyl-alanine (PAL) in the solution and solid phase, namely, NAP, is demonstrated. The method constructs functionally diverse and highly stable N-alkylated conjugates with various peptides. Notably, conjugations in the solid phase offered a more economical process. The method can provide the opportunity for dual labeling along with a cysteine handle in a peptide chain. Finally, we showcased that the antiproliferative activities of the p53 peptide (MDM2 inhibitor) could be 2-fold enhanced via NAP conjugation with the RGD peptide (selective integrin binder).

中文翻译：

通过吡啶基丙氨酸的 N-烷基化引入化学选择性肽缀合：溶液和固相应用

证明了一种通过溶液和固相中吡啶基丙氨酸 (PAL) 的后期N-烷基化形成的新型化学选择性肽缀合，即 NAP。该方法用各种肽构建功能多样且高度稳定的N-烷基化缀合物。值得注意的是，固相缀合提供了更经济的过程。该方法可以提供与肽链中的半胱氨酸手柄一起进行双重标记的机会。最后，我们展示了 p53 肽（MDM2 抑制剂）的抗增殖活性可以通过 NAP 与 RGD 肽（选择性整联蛋白结合剂）缀合而增强 2 倍。

更新日期：2024-09-13

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