Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-dmap and 6-dmn
Nat Protoc. 2007-12-01; 2(12): 3219-3225
DOI: 10.1038/nprot.2007.444
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1. Nat Protoc. 2007;2(12):3219-25.
Synthesis of anhydride precursors of the environment-sensitive fluorophores
4-DMAP and 6-DMN.
Sainlos M(1), Imperiali B.
Author information:
(1)Department of Chemistry, Massachusetts Institute of Technology, 77
Massachusetts Avenue, Cambridge, Massachusetts 02139-4307, USA.
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.
DOI: 10.1038/nprot.2007.444
PMID: 18079722 [Indexed for MEDLINE]