Abstract
This protocol describes the synthesis of cyclic anhydride precursors of the environment-sensitive fluorophores 4-dimethylaminophthalimide (4-DMAP) and 6-dimethylaminonaphthalimide (6-DMN). The condensation of these anhydrides with a primary amino group confers on molecules of interest solvatochromic properties. In particular, two strategies for the insertion of the chromophores into peptides are presented in two companion protocols. The anhydride syntheses can be completed on the gram scale in 2 d for the 4-DMAP precursor and 10–15 d for the 6-DMN precursor.
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Sainlos, M. & Imperiali, B. Tools for investigating peptide–protein interactions: peptide incorporation of environment-sensitive fluorophores through SPPS-based 'building block' approach. Nat. Protoc. 2, 3210–3218 (2007).
Acknowledgements
This research was supported by NSF CHE-0414243 (B.I.) and the Cell Migration Consortium (GM064346). The award of a Marie Curie Fellowship to M.S. is also gratefully acknowledged.
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The authors declare that a patent on the environment–sensitive fluorophores is pending: “Fluorescent Probes for Biological Studies” by Imperiali et al. US Patent Application serial No. 11/106,349, filed April 13, 2005, pending.
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Sainlos, M., Imperiali, B. Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN. Nat Protoc 2, 3219–3225 (2007). https://doi.org/10.1038/nprot.2007.444
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DOI: https://doi.org/10.1038/nprot.2007.444
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