58889-73-9Relevant academic research and scientific papers
Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling
Freas, Dylan J.,Fu, Gregory C.,Yang, Ze-Peng
, p. 8614 - 8618 (2021/06/28)
Interest in unnatural α-Amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chemistry to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enanti
A rapid reaction releasing the carboxyl terminal residues of peptides
Yagisawa, Shiroki,Urakami, Masako
, p. 7557 - 7560 (2007/10/03)
Alcoholysis of peptide oxazolones in alcohols containing dilute acid, such as 0.02M HCl, gives the C-terminal amino acid and the ester of the shortened peptide within 10 minutes at room temperature in 30-70% yields. This together with the finding that the peptide oxazolones can be formed within 3 minutes with alkylchloroformates enables the rapid removal of peptide C-terminal residues.
MIXED CARBOXYLIC - CARBONIC ANHYDRIDE METHOD IN PHOSPHONO PEPTIDE SYNTHESIS
Kafarski, Pawel,Lejczak, Barbara
, p. 7387 - 7396 (2007/10/02)
Factors influencing the reaction yields and formation of the side products during coupling of N-carbobenzoxyamino acids with dialkyl or diphenyl aminoalkylphosphonates, by means of mixed anhydryde procedure, were evaluated.The recommended procedure, arising from these studies, involves the use of chloroform/ethyl chloroformate/triethylamine system and delicate warming of the reaction mixture during the coupling step.
PAPAIN-ASSISTED RESOLUTION OF NATURAL AND XENOBIOTIC α-AMINO ACIDS
Moriniere, J. L.,Danree, B.,Lemoine, J.,Guy, A.
, p. 441 - 444 (2007/10/02)
A new and convenient method for the preparation of pure enantiomers of α-amino acids is described.Industrial papain, catalyzes the synthesis of L-Z-amino acid ethyl esters in ethanolic medium, with good yields.These esters are obtained from DL-Z-amino acids with 100percent optical purity.Unreactive D-Z-amino acids are readily isolated from reaction medium.Physical constants of natural and xenobiotic L-Z-amino acid esters and D-Z-amino acids are described.
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
38. Approaches to the Synthesis of Cytochalasans. Part 4. Improved Synthesis of the Tetrahydroisoindoline Subunits Related to the Cytochalasins and Aspochalasins
Schmidlin, Tibur,Bruckhardt, Peter E.,Waespe-Sarcevic, Nada,Tamm, Christoph
, p. 450 - 465 (2007/10/02)
A general scheme for the synthesis of the tetrahydroisoindolinone moiety of naturally occurring cytochalasans and unnatural analogs was developed.The keystep consist of the intermolecular cycloaddition of 4-methylsorbinol (7) to an alkylidene malonic
