ANSA analysis. II. Aminonaphthalenesulfonamides--detecting groups for polysubstrate analysis of proteases

• Published in: Biokhimiia (Moscow, Russia) Vol. 59; no. 10; p. 1521
• Main Authors: Trushkin, A M, Kazantsev, A G, Kuznetsov, N V, Iakhimovich, A D, Moguchaia, G Iu, Rodina, E V, Gridneva, N A, Sharina, I G, Nedospasov, A A
• Format: Journal Article
• Language: Russian
• Published: Russia (Federation) 01-10-1994
• Subjects: Alkylation; Anilino Naphthalenesulfonates; Chromogenic Compounds; Endopeptidases - chemistry; Endopeptidases - metabolism; Substrate Specificity
• ISSN: 0320-9725

The properties and synthetic methods of aminonaphthalenesulfonamides (ANSA) used as detectable groups of protease substrates are described. A list of chemical and physical properties of seventeen 5.1-ANSA with simple substituents is presented. A comparison of condition for the introduction and removal of acyl protecting groups (acetyl, trifluoroacetyl, phthaloyl, carbobenzoxy) used in ANSA synthesis is given. Examples of applicability of nitronaphthalenesulfonamides as intermediate compounds are given. The possibility of ANSA alkylation at both N(C) and N(S) is demonstrated. Substituted ANSA--sulfonylaziridenes--are used for the production of water-soluble derivatives containing the alcoxy group in the sulfonamide fragment. Criteria for the selection of detectable groups for polysubstrate analysis are discussed. Eighteen typical procedures for ANSA synthesis according to the schemes discussed are presented.