Solid phase synthesis of vancomycin mimics

A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-bead SNAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.