78172-93-7Relevant academic research and scientific papers
Protease catalysis mediated by a substrate mimetic: A novel enzymatic approach to the synthesis of carboxylic acid amides
Guenther, Robert,Bordusa, Frank
, p. 463 - 467 (2007/10/03)
We present a protease-based method for the coupling of non-coded and non-amino-acid-derived amines with carboxy components. The key feature of this approach is the combination of the substrate-mimetic strategy with the ability of the cysteine protease clostripain to accept a wide spectrum of amines. Firstly, we tested the use of the 4-guanidinophenyl ester leaving group to mediate acceptance of non-coded and non-amino-acid-derived acyl residues. This employed β-amino acid and simple carboxylic acid moieties as acyl donors, and several amino acid and peptide units as acyl acceptors. The study was completed by the use of non-amino-acid-derived acyl acceptors comprising simple amines, amino alcohols, and diamines. The results indicate that the approach presented is a useful strategy for the synthesis of peptide isosteres, peptide analogues, and organic amides. These last open a new range of synthetic applications of proteases completely beyond peptide synthesis, achieving efficient and selective acylations of non-amino-acid-derived amines under extraordinarily mild reaction conditions.
A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
Watanabe, Yutaka,Mukaiyama, Teruaki
, p. 285 - 288 (2007/10/02)
Various carboxamides and peptides are prepared in good yields by treatment of free acids and amines in H2O-dichloromethane or aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide.Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.
