A General Method for the Preparation of Internally Quenched Fluorogenic Protease Substrates Using Solid-Phase Peptide Synthesis

Linda L. Maggiora, Clark W. Smith, Zhong Yin Zhang

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

A general scheme for obtaining a fluorescent donor/acceptor peptide substrate via solid-phase synthesis methodology is presented. The key feature of this method is the design of a glutamic acid derivative that has been modified on the carboxyl side chain with a 5- [(2′-aminoethyl) - amino] naphthelenesulfonic acid (EDANS) to create a fluorescent donor moiety that can be incorporated near the C-terminus of the peptide substrate. The corresponding fluorescent acceptor group containing a 4- [[4- (dimethylamino)phenyl] azo] benzoic acid (DABCYL) can then be attached to the resin-bound peptide at the N-terminus while all side-chain groups are still fully protected. Substrates for renin and HIV proteinase are synthesized as examples.

Original languageEnglish (US)
Pages (from-to)3727-3730
Number of pages4
JournalJournal of Medicinal Chemistry
Volume35
Issue number21
DOIs
StatePublished - Oct 1 1992
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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