Synthesis of 4-(Fmoc-aminoacyloxymethyl)phenoxyacetic Acids for Use in Solid-Phase Peptide Synthesis

Nikos Zinieris; Stella Kokinaki; Leondios Leondiadis; Nikolas Ferderigos

doi:10.1055/s-2006-942485

PAPER

Synthesis of 4-(Fmoc-aminoacyloxymethyl)phenoxyacetic Acids for Use in Solid-Phase Peptide Synthesis

Nikos Zinieris^a, Stella Kokinaki^a, Leondios Leondiadis^b, Nikolas Ferderigos*^a
^a Laboratory of Organic Chemistry, Chemistry Department, University of Athens, 157 71 Athens, Greece
^b Mass Spectrometry and Dioxine Analysis Lab, IRRP, National Centre for Scientific Research ‘Demokritos’, 153 10 Athens, Greece
Fax: +30(210)7274761; e-Mail: nferder@chem.uoa.gr;

Abstract

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Abstract

The synthesis of 4-(Fmoc-aminoacyloxymethyl)phenoxyacetic acids was achieved in high yield by the reaction of Fmoc-amino acids with (4-iodomethylphenoxy)acetic acid 2-oxo-2-phenylethyl ester. The removal of the temporary protecting group, phenacyl ester, was effectively achieved by reductive cleavage with magnesium turnings.

Key words

solid-phase synthesis - magnesium - peptides

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