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Solid Phase Synthesis of Phosphopeptides Incorporating 2,2-Dimethyloxazolidine Pseudoproline Analogs: Evidence for trans Leu-Pro Peptide Bonds in Stat3 Inhibitors

Coleman, David R. ; Kaluarachchi, Kumaralal ; Ren, Zhiyong ; Chen, Xiaomin ; McMurray, John S.

International journal of peptide research and therapeutics, 2008-03, Vol.14 (1), p.1-9 [Periódico revisado por pares]

Dordrecht: Springer Netherlands

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  • Título:
    Solid Phase Synthesis of Phosphopeptides Incorporating 2,2-Dimethyloxazolidine Pseudoproline Analogs: Evidence for trans Leu-Pro Peptide Bonds in Stat3 Inhibitors
  • Autor: Coleman, David R. ; Kaluarachchi, Kumaralal ; Ren, Zhiyong ; Chen, Xiaomin ; McMurray, John S.
  • Assuntos: Animal Anatomy ; Biochemistry ; Biomedical and Life Sciences ; Biosynthesis ; Cytokines ; Histology ; Life Sciences ; Molecular Medicine ; Morphology ; Oncology ; Peptides ; Pharmaceutical Sciences/Technology ; Pharmacology ; Pharmacology/Toxicology ; Polymer Sciences ; Signal transduction
  • É parte de: International journal of peptide research and therapeutics, 2008-03, Vol.14 (1), p.1-9
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: To answer the question of whether the conformation of the Leu-Pro bond is cis or trans in Ac-pTyr-Leu-Pro-Gln-Thr-Val-NH 2 when complexed with the SH2 domain of Stat3, we substituted 2,2-dimethyloxazolidines derived from serine (Ser(Ψ Me,Me pro)) and threonine (Thr(Ψ Me,Me pro)) for proline. The 2,2-dimethyloxazolidine and 2,2-dimethylthiazolidine pseudoproline (ΨPro) analogs induce predominantly cis Xxx-ΨPro peptide bonds. As these ΨPro analogs are acid-labile, the phosphopeptides were synthesized using Fmoc-based SPPS using unprotected phosphotyrosine and 4-hydroxybenzoate as the linker that allowed release from the support by alkaline ammonolysis, conditions that kept the oxazolidine rings intact. Incorporation of Ser(Ψ Me,Me pro) resulted in 69% cis Leu-ΨPro bond content in aqueous solution whereas that for Thr(Ψ Me,Me pro) analog was 63%. Affinities for Stat3 were 3–5 fold lower than the lead compound and were inversely correlated with cis content. Thus we conclude that the Leu-Pro peptide bond is trans when the peptide is bound to Stat3.
  • Editor: Dordrecht: Springer Netherlands
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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