Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN.
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.
Sainlos
Matthieu
M
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139-4307, USA.
Imperiali
Barbara
B
D015761:4-Aminopyridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D053644:Naphthalimides / Q000737:chemistry*
C499819:6-N,N-dimethylamino-2,3-naphthalimide; D005456:Fluorescent Dyes; D007094:Imides; D009281:Naphthalenes; D053644:Naphthalimides; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine