Synthesis of 2-(trimethylsilyl)ethyloxycarbonylamino acids and their use in peptide chemistry.

B Wünsch, L Moroder, O Keller

Index: Hoppe. Seylers. Z. Physiol. Chem. 362 , 1289, (1981)

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Abstract

2-(Trimethylsilyl)ethyl-4-nitrophenyl carbonate has been prepared as a new reagent for the introduction of the 2-(trimethylsilyl)ethyloxycarbonyl group into amino acids or amino acid derivatives. The resulting N alpha-protected amino acids were found to represent suitable intermediates for the synthesis of peptides. The amino-protecting group proved to be stable under the usual conditions of peptide synthesis and readily cleaved in selective conditions via fluoride ion-mediated fragmentation.