Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments

Guilford Jones, Lily N. Lu, Valentine Vullev, David J. Gosztola, Scott R. Greenfield, Michael R Wasielewski

Research output: Contribution to journal › Article

37 Citations (Scopus)

Abstract

The (nitro)pyrenesulfonamide group has been attached to the N-terminus of tryptophan and tryptophan-containing peptides. Intramolecular electron transfer between pyrene and Trp indole side chains, observed by fluorescence quenching and laser flash photolysis, depends on the spacing between Pyr and Trp moieties and the strength of the electron acceptor.

Original languageEnglish
Pages (from-to)2385-2390
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume5
Issue number20
DOIs
Publication statusPublished - Oct 19 1995

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Tryptophan
Labeling
Electrons
Peptides
Photolysis
Quenching
Lasers
Fluorescence
Experiments
indole
pyrene
tryptophyltryptophan

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments. / Jones, Guilford; Lu, Lily N.; Vullev, Valentine; Gosztola, David J.; Greenfield, Scott R.; Wasielewski, Michael R.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 5, No. 20, 19.10.1995, p. 2385-2390.

Research output: Contribution to journal › Article

Jones, G, Lu, LN, Vullev, V, Gosztola, DJ, Greenfield, SR & Wasielewski, MR 1995, 'Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments', Bioorganic and Medicinal Chemistry Letters, vol. 5, no. 20, pp. 2385-2390. https://doi.org/10.1016/0960-894X(95)00416-Q
Jones G, Lu LN, Vullev V, Gosztola DJ, Greenfield SR, Wasielewski MR. Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments. Bioorganic and Medicinal Chemistry Letters. 1995 Oct 19;5(20):2385-2390. https://doi.org/10.1016/0960-894X(95)00416-Q
Jones, Guilford ; Lu, Lily N. ; Vullev, Valentine ; Gosztola, David J. ; Greenfield, Scott R. ; Wasielewski, Michael R. / Photoinduced electron transfer for pyrenesulfonamide conjugates of tryptophan-containing peptides. Mitigation of fluoroprobe behavior in N-terminal labeling experiments. In: Bioorganic and Medicinal Chemistry Letters. 1995 ; Vol. 5, No. 20. pp. 2385-2390.
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