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Preparation and Some Properties of Maleimido Acids and maleoyl derivatives of peptides
Author(s) -
Keller Oskar,
Rudinger Josef
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580224
Subject(s) - maleimide , chemistry , moiety , amide , hydrolysis , amino acid , peptide , thiol , reactivity (psychology) , conjugate , aqueous solution , organic chemistry , combinatorial chemistry , biochemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology
Abstract N‐Alkoxycarbonylmaleimides 3 have been prepared and used to convert amino acids to maleimido acids (6–8) in aqueous solution. The carboxyl group of maleimido acids can be activated for amide or peptide synthesis ( e.g. , in the N‐succinimidyl esters 10); t ‐butyl‐based protecting groups can be cleaved without damage to the maleimide moiety. Peptides carrying maleimide groups are accessible either from the maleimido acids ( e.g. , 11b, 15) or by direct maleoylation ( e.g. , 16b). The maleoyl group can be cleaved off by successive mild alkaline and acid hydrolysis or by hydrazinolysis. The reactivity of maleimides toward thiol groups suggests the use of maleimido acids and maleoylpeptides for preparing a wide range of conjugates of biochemical interest.