A six-step reaction sequence is described for the preparation of compound 1 (NTA3-DTDA), a membrane-penetrating and potent chelator that can be incorporated into liposomes and plasma membrane vesicles containing antigens and thus allowing targeted delivery of such assemblies to a variety of cells for the purposes of eliciting anti-tumour responses. Full spectroscopic characterization of this dendritic-type compound as well as certain of its precursors is reported.

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β-Nitro-α-amino acids, that are readily accessible through either the reaction of bromoglycine derivatives with alkyl nitronates or the three-component coupling of amines, nitroalkanes and glyoxalate in aqueous base, are easily converted to the corresponding N-t-Boc-amino acids. These undergo solid-phase Merrifield peptide synthesis, with elimination of nitrous acid, either during or subsequent to cleavage of the peptide from the resin, converting the nitro amino acids to dehydro amino acid residues. The method has been applied successfully with two β,β-disubstituted nitro amino acids and N-methyl-β-nitronorvaline, but failed with β-nitroalanine.