126306-89-6Relevant academic research and scientific papers
UTILISATION DES HYDROLASES EN CHIMIE ORGANIQUE: SYNTHESE DE LIAISONS ESTER ET AMIDE CATALYSEE PAR LA PAPAINE INDUSTRIELLE
Moriniere, Jean-Luc,Danree, Bernard,Guy, Alain
, p. 347 - 358 (2007/10/02)
The use of hydrolases in organic chemistry: synthesis of amide and ester bonds catalyzed by industrial papain.Industrial papain, which is readily available, catalyzed the synthesis of L-Z-alanine ethyl ester (L-ZAEt) in organic medium, under different conditions, with good yields.L-ZAEt was obtained from DL-Z-alanine with 100 percent optical purity.We studied the effects of pH, the solvent/substrate and papain/substrate ratios and the type of organic solvent added, on the L-ZAEt yield.Unreactive D-ZA was also easily isolated from the aqueous phase with good optical purity.This attractive method has been applied to other N-Z-amino acid esters with the same succes.This procedure has been developed for the preparation of peptides using carboxylic or phosphonic substrates.These peptides have anti-bacterial activity. enzymatic catalysis / papain / chymopapain / stereospecific esterification of carboxylic amino acids / dipeptides / phosphonopeptides / anti-bacterial activity
STUDIES ON THE SYNTHESIS OF CHEMOTHERAPEUTICS. PART XI. SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF PHOSPHONOPEPTIDES
Kametani, Tetsuji,Kigasawa, Kazuo,Hiiragi, Mineharu,Wakisaka, Kikuo,Haga, Seiji,et al.
, p. 1205 - 1242 (2007/10/02)
A variety of phosphonopeptides, shown in 2 as a general formula, containg natural and/or unnatural amino acids were synthesized, and their in vitro antibacterial activities were examined.N-Protected amino acids were condensed with 1-amino-ethylphosphonic acid or its ester followed by deprotection and hydrolysis to give the requisite phosphonopeptides.Several compounds showed higher levels of activity against certain members of Gram-negative bacteria than those of Alafosfalin (1) as the standard phosphonopeptide.A brief discussion on structure-activity relationships is also described.
