Synthesis of 2-(trimethylsilyl)ethyloxycarbonylamino acids and their use in peptide chemistry.
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.
D000596:Amino Acids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000138:chemical synthesis*; D012825:Silicon / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis*
D000596:Amino Acids; D007202:Indicators and Reagents; D010455:Peptides; D014297:Trimethylsilyl Compounds; D012825:Silicon