Preparation of a conjugation-ready thiol responsive molecular switch

Brandon Tautges, Victor Or, Joel Garcia, Jared T. Shaw, Angelique Y. Louie

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

In this work we synthesize molecular switches that are responsive to cysteine, homocysteine, and glutathione; three redox systems that make up the majority of the body's antioxidant defenses. Synthesized spiropyran isomers with conjugation-ready linkages showed good selectivity of response to these major antioxidant thiols over nucleophilic amino acids; however the position of the linking group can affect selectivity and reversibility of the switching response. An isomer with selectivity for cysteine against GSH and Hcy was identified.

Original languageEnglish (US)
Pages (from-to)6569-6573
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number47
DOIs
StatePublished - Nov 25 2015

Keywords

  • Colorimetric sensor
  • Spiropyran
  • Thiol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Tautges, B., Or, V., Garcia, J., Shaw, J. T., & Louie, A. Y. (2015). Preparation of a conjugation-ready thiol responsive molecular switch. Tetrahedron Letters, 56(47), 6569-6573. https://doi.org/10.1016/j.tetlet.2015.10.019