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 Citations (Scopus)

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

Fingerprint

Sulfhydryl Compounds
Isomers
Cysteine
Antioxidants
Switches
Homocysteine
Oxidation-Reduction
Glutathione
Amino Acids
spiropyran

Keywords

  • Colorimetric sensor
  • Spiropyran
  • Thiol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

Preparation of a conjugation-ready thiol responsive molecular switch. / Tautges, Brandon; Or, Victor; Garcia, Joel; Shaw, Jared T.; Louie, Angelique Y.

In: Tetrahedron Letters, Vol. 56, No. 47, 25.11.2015, p. 6569-6573.

Research output: Contribution to journalArticle

Tautges, B, Or, V, Garcia, J, Shaw, JT & Louie, AY 2015, 'Preparation of a conjugation-ready thiol responsive molecular switch', Tetrahedron Letters, vol. 56, no. 47, pp. 6569-6573. https://doi.org/10.1016/j.tetlet.2015.10.019
Tautges, Brandon ; Or, Victor ; Garcia, Joel ; Shaw, Jared T. ; Louie, Angelique Y. / Preparation of a conjugation-ready thiol responsive molecular switch. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 47. pp. 6569-6573.
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