共查询到20条相似文献，搜索用时 15 毫秒
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Anaïs F. M. Noisier Magnus J. Johansson Laurent Knerr Martin A. Hayes William J. Drury Eric Valeur Lara R. Malins Ranganath Gopalakrishnan 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(52):19272-19278
The late‐stage functionalization (LSF) of peptides represents a valuable strategy for the design of potent peptide pharmaceuticals by enabling rapid exploration of chemical diversity and offering novel opportunities for peptide conjugation. While the C(sp2)?H activation of tryptophan (Trp) is well documented, the resurgence of radical chemistry is opening new avenues for the C?H functionalization of other aromatic side‐chains. Herein, we report the first example of LSF at C2 of histidine (His) utilizing a broad scope of aliphatic sulfinate salts as radical precursors. In this work, the exquisite selectivity for histidine functionalization was demonstrated through the alkylation of complex unprotected peptides in aqueous media. Finally, this methodology was extended for the installation of a ketone handle, providing an unprecedented anchor for selective oxime/hydrazone conjugation at histidine. 相似文献
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《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(28):8338-8342
Penetratin (RQIKIWFQNRRMKWKK) enters cells by different mechanisms, including membrane translocation, thus implying that the peptide interacts with the lipid bilayer. Penetratin also crosses the membrane of artificial vesicles, depending on their phospholipid content. To evaluate the phospholipid preference of penetratin, as the first step of translocation, we exploited the benzophenone triplet kinetics of hydrogen abstraction, which is slower for secondary than for allylic hydrogen atoms. By using multilamellar vesicles of varying phospholipid content, we identified and characterized the cross‐linked products by MALDI‐TOF mass spectrometry. Penetratin showed a preference for negatively charged (vs. zwitterionic) polar heads, and for unsaturated (vs. saturated) and short (vs. long) saturated phospholipids. Our study highlights the potential of using benzophenone to probe the environment and insertion depth of membranotropic peptides in membranes. 相似文献
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Sheereen Majd Michael Mayer 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2005,117(41):6855-6858
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Ilya Koltover Sanjukta Sahu Nicolynn Davis 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2004,116(31):4126-4129