553668-45-4

Upstream product

• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 110-60-1 1,4-diaminobutane 
• 63-91-2 L-phenylalanine 
• 1161-13-3 N-Cbz-L-Phe 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 81638-49-5 1,4-bis(Phe-amino)butane 

Relevant academic research and scientific papers

Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids

A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic acids. Those bis(amino amide) receptors contain different structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSAs, depends on those structural variables. The influence of aminoacid side chain and the nature of the aliphatic spacer are important parameters to obtain good chiral discriminations. The results obtained clearly show the chiral recognition abilities of these bis(amino amide) ligands and suggest their advantageous use as chiral solvating agents for carboxylic acids. The binding between bis(amino amides) and carboxylic acids has been studied by ESI-MS, NMR, DSC, and molecular modeling. The data suggest that enantiodiscrimination involves the formation of an ionic pair after proton transfer from the carboxylic substrate to the bis(amino amides).

A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral π-channels

The crystal structure of a simple peptidomimetic compound, derived from phenylalanine, shows the formation of a nanoporous architecture containing monodimensional π-channels with the aromatic rings as the exclusive components of the chiral channel walls. The Royal Society of Chemistry 2010.

Optically active tropocoronands having amino acid residues in linker chains: Syntheses, metal coordination properties, and their abilities as an asymmetric catalyst

Optically active tropocoronands (7) having l-amino acid moieties were synthesized by stepwise and one-pot reactions of tropolone derivatives with amino acid linker chains. The coordination styles of their Ni(II) and Pd(II) complexes and the abilities as an asymmetric catalyst were investigated.

Efficient macrocyclization of U-turn preorganized peptidomimetics: The role of intramolecular H-bond and solvophobic effects

Simple peptidomimetic molecules derived from amino acids were reacted with meta- and parabis(bromomethyl) benzene in acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by 1H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization. The role played by intramolecular hydrogen-bonding and solvophobic effects in the presence of folded conformations is analyzed.

Homogeneous and supported copper complexes of cyclic and open-chain polynitrogenated ligands as catalysts of cyclopropanation reactions

Cu(I) and Cu(II) complexes of cyclic and open-chain polyaza compounds have been tested as catalysts in the benchmark cyclopropanation reaction of styrene with ethyl diazoacetate. In general, only small amounts of copper are needed to promote the reaction. The catalytic activity depends on the structure of the ligand, e.g. amine-amides are more efficient than polyamines, and on the oxidation state of copper, Cu(II) being more active than Cu(I). Given that Cu(I) is the active species, these changes of behavior must be related to the stabilities of the complexes. The nature of the counterion also has a noticeable influence on the catalytic activity, the role of which is discussed. XAS measurements suggest the formation of oligomeric species. Some of the chiral ligands lead to small enantiomeric excesses, open-chain ligands can easily be supported on organic polymers and their complexes can be used as catalysts. Furthermore, cyclic and acyclic complexes can be supported on clays by cation exchange and the solids obtained tend to promote the reaction with a decrease in the trans/cis ratio.