60668-15-7

Upstream product

• 70858-86-5 dimethyl [(N-benzyloxycarbonyl-L-phenylalanyl)amino]-methylphosphonate 
• 3588-57-6 Z-DL-Phe-OH 
• 1161-13-3 N-Cbz-L-Phe 
• 82610-83-1 ester ethylique de l'acide (N-benzyloxycarbonyl)-L-phenylalanyl-aminomethylphosphonique 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 60668-59-9 [(N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanyl)amino]-methylphosphonic acid 
• 60668-62-4 {[(S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-methyl}-phosphonic acid; compound with benzylamine 
• 60668-60-2 (L-phenylalanyl-L-phenylalanylamino)-methylphosphonic acid 
• 60668-63-5 (L-alanyl-L-phenylalanylamino)-methylphosphonic acid 

Relevant academic research and scientific papers

PHOSPHONODIPEPTIDES. SYNTHESIS BY HOBt/DCC METHOD, MASS SPECTRA OF THE PROTECTED AND 1H NMR OF THE UNPROTECTED PHOSPHONODIPEPTIDES

Phosphonodipeptides containing aminomethylphosphonic and 1-aminoethylphosphonic acids were synthesized by the active ester method using N-hydroxybenztriazole and DCC.Fragmentation in electron ionization mass spectra (EI/MS) of protected phosphonodipeptide

UTILISATION DES HYDROLASES EN CHIMIE ORGANIQUE: SYNTHESE DE LIAISONS ESTER ET AMIDE CATALYSEE PAR LA PAPAINE INDUSTRIELLE

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 XIII. SYNTHESIS AND BIOLOGICAL STUDIES ON PHOSPHONOPEPTIDES HAVING ALKYL-, PHENYL-, AND HETEROCYCLIC SUBSTITUENTS.

New antibacterial phosphonopeptides (3) were synthesized in order to improve the stability against hydrolysis by peptidase and the antibacterial spectra.Synthesis of them was accomplished by condensation of the N-carbobenzoxyamino acid with diethyl aminoalkylphosphonate followed by deprotection and hydrolysis.The antibacterial activity was evaluated in a defined medium and the stability against hydrolysis by rat liver homogenates was examined.Chemical modification of the N-terminal amino acid moiety of the phosphonopeptide containing sulfur or oxygen atom at β- or γ-position of the N-terminal α-amino acid residue lost rapidly their in vivo activity in spite of the high in vitro activity.The para substituted phenylalanyl-1-aminoethyl-phosphonic acids showed higher stability and slightly lower activity compared with those of the corresponding ortho- and meta-substituted isomers.Some of these para-substituted compounds (e.g. 9β, 10β, and 19β) exhibited the same level of the biological activity as that of Alafosfalin (1) in potency of the activity, broadness of the spectrum, and the serum level in mice after peroral administration.Phosphonopeptides consisted of unnatural amino acids and aminomethylphosphonic acid showed generally the extended spectra and activities, but these compounds were very fragile to hydrolysis by peptidase.None of phosphonopeptides containing 2-aminoethylphosphonic acid had the activity.

Peptide derivatives of phosphonic and phosphinic acids and intermediates therefor

The present disclosure relates to peptide derivatives. More particularly, the disclosure is concerned with peptide derivatives of phosphonic and phosphinic acids, a process for the manufacture thereof and pharmaceutical preparations containing same.