Synthesis of novel nucleo-β-amino acids and nucleobase-functionalized β-peptides

Article abstract of DOI:10.1002/ejoc.200300269

Four novel β-amino acids bearing the canonical nucleobases guanine, cytosine, adenine, and thymine in the side chain, are synthesized starting from Boc-L-aspartic acid 4-benzyl ester. The syntheses are accomplished in six steps by the nucleophilic substitution of (S)-β -(tert-butoxycarbonylamino)-δ-bromopentanoic acid benzyl ester with the corresponding nucleobase derivative as the key step. The guaninyl and cytosinyl β-amino acids were built into β-peptides that were studied by temperature-dependent CD and UV spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.