Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN

Matthieu Sainlos; Barbara Imperiali

doi:10.1038/nprot.2007.444

Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN

Nat Protoc. 2007;2(12):3219-25. doi: 10.1038/nprot.2007.444.

Authors

Matthieu Sainlos¹, Barbara Imperiali

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139-4307, USA.

PMID: 18079722
DOI: 10.1038/nprot.2007.444

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.

MeSH terms

4-Aminopyridine / analogs & derivatives*
4-Aminopyridine / chemical synthesis
Fluorescent Dyes / chemical synthesis*
Imides / chemistry*
Molecular Structure
Naphthalenes / chemistry*
Naphthalimides / chemistry*

Substances

6-N,N-dimethylamino-2,3-naphthalimide
Fluorescent Dyes
Imides
Naphthalenes
Naphthalimides
4-Aminopyridine
4-dimethylaminopyridine