Application of the Trt and Fmoc groups for the protection of polyfunctional α-amino acids

Published on 25.01.2017

Abstract: Ditrityl amino acids Trt-Lys(Trt)-OH (Trt = CPh3), Trt-Orn(Trt)-OH, Trt-Ser(Trt)-OH, and Trt-Hse(Trt)-OH were prepared and used in the synthesis of trityl-protected peptides, e.g., Trt-Ser(Trt)-Phe-NH2.

Barlos, Kleomenis; Mamos, Petros; Papaioannou, Dionysios; Patrianakou, Stella; Sanida, Chariklia; Schaefer, Wolfram.

Liebigs Annalen der Chemie 1987; 12: 1025-30.

Abstract:
Ditrityl amino acids Trt-Lys(Trt)-OH (Trt = CPh3), Trt-Orn(Trt)-OH, Trt-Ser(Trt)-OH, and Trt-Hse(Trt)-OH were prepared and used in the synthesis of trityl-protected peptides, e.g., Trt-Ser(Trt)-Phe-NH2. Selective detritylation of the above amino acid derivatives and ditrityl peptides was achieved with 1% CF3CO2H in CH2Cl2. The resulting N-detritylated amino acids were converted into the corresponding Nα-Fmoc (Fmoc = fluorenylmethyloxycarbonyl) derivatives under Schotten-Baumann conditions using Fmoc-Cl.