Volume 7, Number 6, 347-351, DOI: 10.1023/A:1013016323676

An efficient Fmoc strategy for the rapid synthesis of peptide para-nitroanilides

G. Abbenante, D. Leung, T. Bond and D.P. Fairlie

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Abstract

A new strategy has been developed for the rapid synthesis ofpeptide para-nitroanilides (pNA). The method involves derivatization of commercially available tritylchloride resin(TCP-resin) with 1,4-phenylenediamine, subsequent coupling withdesired amino acids by the standard Fmoc protocol, and oxidationof the intermediate para-aminoanilides (pAA) with Oxone®. This procedure allows easy assembly of the desired para-aminoanilides (pAA) on standard resin and efficient oxidation and purification of the corresponding para-nitroanilides (pNA). The method allows easy access to any desired peptide para-nitroanilides, which are useful substrates for the characterization and study of proteolytic enzymes.

chromogenic substrates - oxidation - Oxone® - para-nitroanilides - solid-phase synthesis

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