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; M. R. Wasielewski

doi:10.1016/0960-894X(95)00416-Q

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, M. R. Wasielewski

Northwestern University

Research output: Contribution to journal › Article › peer-review

43 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 language	English
Pages (from-to)	2385-2390
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	5
Issue number	20
DOIs	https://doi.org/10.1016/0960-894X(95)00416-Q
Publication status	Published - Oct 19 1995

ASJC Scopus subject areas

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

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Jones, G., Lu, L. N., Vullev, V., Gosztola, D. J., Greenfield, S. R., & Wasielewski, M. R. (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, 5(20), 2385-2390. https://doi.org/10.1016/0960-894X(95)00416-Q

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, M. R.

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

Research output: Contribution to journal › Article › peer-review

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, Guilford ; Lu, Lily N. ; Vullev, Valentine ; Gosztola, David J. ; Greenfield, Scott R. ; Wasielewski, M. 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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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.",

author = "Guilford Jones and Lu, {Lily N.} and Valentine Vullev and Gosztola, {David J.} and Greenfield, {Scott R.} and Wasielewski, {M. R.}",

note = "Funding Information: Acknowledgements. Support of this research by the Department of Energy, Office of Basice Energy Science, Division of Chemical Science, is gratefully acknowledged. The authors wish to thank also Dr. Frank Mari (Florida Atlantic University) and Dr. Churl Oh for assistance in peptide conformational analysis.",

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AU - Greenfield, Scott R.

AU - Wasielewski, M. R.

N1 - Funding Information: Acknowledgements. Support of this research by the Department of Energy, Office of Basice Energy Science, Division of Chemical Science, is gratefully acknowledged. The authors wish to thank also Dr. Frank Mari (Florida Atlantic University) and Dr. Churl Oh for assistance in peptide conformational analysis.

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AB - 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.

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

Abstract

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