Squaric esters as peptide stapling reagents.

Autor: Wayment AX; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Johnson NC; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Moreno MR; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Stewart C; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Felix BM; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Lambert I; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Traynor SA; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Nielson PM; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Lofgreen GQ; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Smith SL; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Newton MP; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Tretbar JW; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Nygaard JML; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Harrell KG; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Kinghorn MJ; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA., Michaelis DJ; Department of Chemsitry and Biochemistry, Brigham Young University, Provo, UT, USA.
Jazyk: angličtina
Zdroj: Tetrahedron letters [Tetrahedron Lett] 2024 Apr 28; Vol. 140. Date of Electronic Publication: 2024 Mar 29.
DOI: 10.1016/j.tetlet.2024.155010
Abstrakt: We report that squaric esters can serve as bifunctional reagents for selective peptide stapling reactions. Formation of the squaric amide staple occurs under mild conditions with amine-containing side chains. We show that short resin-bound peptides are readily stapled on solid phase and that stapling can occur at various relative positions along the peptide and with various amine tether lengths (e.g. Lysine, ornithine, etc). The squaric amide staples are stable to strong acid conditions used to cleave the stapled peptide from the resin and the stapled peptides show an increase in helicity as analyzed through circular dichroism.
Competing Interests: Conflicts of interest The authors declare that there are no financial conflicts of interest with the present work. Declaration of interests The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: David J Michaelis reports financial support was provided by National Institutes of Health. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Databáze: MEDLINE
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