Biogenesis of the N-Hydroxyamide Bond

The first methods for synthesis of N-hydroxyamino acid were developed as early as the end of the last century (7) but only after 1958 (79) did this subject again arouse interest. The difficulties caused by the instability of N-hydroxy amino acids were the reason for only occasional work of most authors in this field. 

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The biogenesis of the N-hydroxyamide bond is an interesting problem 115). That it may involve oxidation of the a- or co-amine group of an amino acid to a hydroxylamine derivative (Scheme 14, path a) was observed in the biosynthesis of ferrichrome (5) 116), hadacidin (13) (25, 117) and aerobactin (8) 118). 

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