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

43 Citations (Scopus)

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
StatePublished - 1992
Externally publishedYes

Fingerprint

Solid-Phase Synthesis Techniques
Fluorescent Dyes
Peptide Hydrolases
Peptides
Substrates
Glutamates
HIV Protease
Angiotensinogen
Benzoic Acid
Resins
Amino Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A general method for the preparation of internally quenched fluorogenic protease substrates using solid-phase peptide synthesis. / Maggiora, Linda L.; Smith, Clark W.; Zhang, Zhong-Yin.

In: Journal of Medicinal Chemistry, Vol. 35, No. 21, 1992, p. 3727-3730.

Research output: Contribution to journalArticle

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