Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors

Benjamin H. Rotstein, Rida Mourtada, Shana O. Kelley, Andrei K. Yudin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme).

Original languageEnglish (US)
Pages (from-to)12257-12261
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number44
DOIs
StatePublished - Oct 24 2011
Externally publishedYes

Keywords

  • fluorescent probes
  • isocyanides
  • macrocycles
  • multicomponent reactions
  • peptides
  • solvatochromism

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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