Hydroxylamine Analogs and Derivatives of Amino Acids. Aminooxy Acids

Abstract

This chapter provides a review of researches in the field of aminooxy acids and related compounds. The first syntheses of aminooxy acids were described about 120 years ago. The first natural aminooxy acids and their derivatives, like canaline, canavanine and the antibiotic cycloserine, were discovered in the thirties and fifties of last century. Their first peptides were prepared in the sixties. In recent years this field gained increasing interest due to the special properties of peptides glycosides and glycopeptides containing aminooxy acids. These biomimetic compounds include aminooxy acids incorporated in biologically active macromolecules, either inside the chains or in terminal positions. The latter derivatives are used for ligation of functional groups resulting in biological probes, biosensors and and other useful devices. The free aminooxy group in such chains enables the facile prepration of bioconjugates, attachment to solid surfaces, modifications of recombinant proteins, preparing various vaccines and more. Peptides, proteins and glycopeptides containing an amidooxy bond exhibit interesting secondary, tertiary and quaternary structures. They reveal new folding properties, resulting in useful biomimetic foldamers for various applications. This chapter includes up to date information on the synthesis, chemical and biological properties of aminooxy acids and their derivatives.