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PubMed1993

N-peptidyl-O-carbamoyl amino acid hydroxamates: irreversible inhibitors for the study of the S2' specificity of cysteine proteinases.

A series of new inhibitors for cysteine proteinases with the general structure Z-Phe-Gly-NHO-CO-Aa (Aa = amino acids) was synthesized and tested as inhibitors of papain-like enzymes (cathepsins S, L, B and papain). Like N-peptidyl-O-acyl hydroxamates the inhibitors inactivate cysteine proteinases by a sulfenamidation of the active site cysteine residue. The most effective inhibitors display second order-rate constants of inactivation in the range of 10(3)-10(4) M-1.s-1. Since the structure of the N-peptidyl-O-carbamoyl amino acid hydroxamates allows the variation of the leaving group this class of inhibitors was used as a new tool for evaluation of the S2' specificity of cysteine proteinases.

Amino Acid Sequence↗
PubMed1995

[Uses of hydroxamic acids and of N-alkoxyimidoyl halides in organic synthesis].

Although N-hydroxyamides (1) have been known for over a century, the chemistry of 1 is still relatively unexplored. The scope of the present review is a survey of the recent advances of the chemistry of 1 and its derivatives, particularly of new chemical reactions having synthetic utility in organic synthesis developed mainly in our laboratory. The review is divided into two sections. The first section described great utility of divalent positively-charged nitrogen species generated from 1 in synthesis. Electrophilic intramolecular cyclization with an acylnitrenium ion generated from an N-methoxy- or an N-allyloxy-N-chloroamide with anhydrous zinc acetate in nitromethane gave an N-methoxy- or an N-allyloxy nitrogen heterocyclic compound, deprotection of which led to formation of the corresponding N-hydroxy compound. Treatment of an N-hydroxy- or an N-methoxy-N-arylamide and the corresponding lactam with various reagents results in removal of the hydroxy or methoxy function and introduction of nucleophiles at the ortho or para position of the aromatic ring. These methodologies were successfully applied by us for the synthesis of the alkaloid, eupolauramine and for new oxindoles related to the alkaloid, gelsemine, by others. The second section described great utility of N-alkoxyimidoyl halides (2) synthesized from 1. Compounds 2 were readily transformed to other functions such as aldehydes, cyanides, and oximes. This methodology was successfully applied to the synthesis of omega-N-hydroxy-alpha-amino acids in optically pure form which were the key intermediates for the synthesis of hydroxamate-containing siderophores.

Hydroxamic Acids↗