58848-63-8

Upstream product

• 55895-89-1 D,L-phenylalanine p-nitrophenyl ester 
• 2578-85-0 p-nitrophenyl N-(benzyloxycarbonyl)-D-phenylalaninate 
• 14009-95-1 p-nitrophenyl N-acetyl-D-phenylalaninate 
• 14009-94-0 p-nitrophenyl N-acetyl-L-phenylalaninate 
• 2578-84-9 p-nitrophenyl N-(benzyloxycarbonyl)-L-phenylalaninate 
• 75531-06-5 2-Decanoylamino-3-phenyl-propionic acid 4-nitro-phenyl ester 
• 75531-06-5 2-Decanoylamino-3-phenyl-propionic acid 4-nitro-phenyl ester 
• 38806-34-7 p-Nitrophenyl 
• 75531-07-6 p-nitrophenyl n-dodecanoyl-D(L)-phenylalaninate 

Downstream Products

• 75531-12-3 N-dodecanoyl-D-phenylalanine 4-nitrophenylester 
• 100-02-7 4-nitro-phenol 
• 673-06-3 D-β-Phenyl-α-alanine 
• 75531-11-2 N-dodecanoyl-L-phenylalanine 4-nitrophenylester 
• 63-91-2 L-phenylalanine 
• 673-06-3 D-(R)-phenylalanine 

Relevant academic research and scientific papers

Capillary electrophoretic separation of enantiomers of amino acids and amino acid derivatives using crown ether and cyclodextrin

The capillary zone electrophoresis using (+)-18-crown-6-tetracarbonic acid as a chiral selector was a suitable method for the enantiomeric separation of racemates of amino acids and of some amino acid derivatives (esters, dipeptides). The influence of the chemical structure of the compounds on the separation was investigated. After optimization of the separation conditions, baseline separations were obtained for most racemates. The addition of acetonitrile and TBAB yielded an improvement of the separation. Improved selectivity was further observed by the application of a cyclodextrin, HP-β-CD, in combination with the crown ether.

Mechanism of Enantioselective Ester Cleavage by Histidine-Containing Dipeptides at a Micellar Interface

Chiral p-nitrophenyl esters derived from the amino acid phenylalanine are cleaved by histidine-containing dipeptides at a micellar interface.High enantioselectivities (up to kL/kD = 30.4 at 0 deg C) are observed.Both the substrates and the catalysts contain an alternating sequence of hydrophobic and hydrophilic groups.Due to the need for hydration of the hydrophilic groups, the hydrophobic groups cannot dissolve completely into the micellar hydrocarbon phase.The kinetic data suggest that the micellar interface is capable of discriminating between transition states that have different hydrophilic and hydrophobic properties.One of the diastereomeric transition states is characterized by a hydrogen bond between the amide CO group of the ester and an NH group of the histidine-containing dipeptide.Upon formation of this hydrogen bond these polar CO and NH groups lose their hydrophilicity which allows the transfer of the adjacent apolar groups to the micellar hydrocarbon phase.The other diastereomeric transition state cannot form this hydrogen bond and the hydrophobic groups remain hydrated.Consequently, the latter transition state is of higher energy.The kinetic data reveal that it is important to prevent steric hinderance between the reactants in order to allow the unhindered formation of the hydrogen bond.

High Stereoselectivity in the Deacylation of p-Nitrophenyl N-Acylphenylalanates by Bilayer Vesicular Systems which include Dipeptide-type Nucleophiles

The deacylation of p-nitrophenyl N-acylphenylalanates with bilayer vesicular systems comprising dipeptide-type nucleophiles and a cationic double chain surfactant resulted in high stereoselectivity (kLcat/kDcat = 29.6 at 25 deg C and 83.6 at 10 deg C) for the deacylation of p-nitrophenyl N-dodecanoylphenylalanate by the catalytic system of N-(N-benzyloxycarbonyl-L-leucyl)-L-histidine and N,N-didodecyl-N,N-dimethylammonium bromide.

Enantioselective Deacylation of Long Chain p-Nitrophenyl N-Acylphenylalanates by N-(N-Dodecanoyl-L-histidyl)-L-leucine and a Cationic Chiral Surfactant

Enhanced enantioselectivity (kcatL/kcatD 5.5-5.7) was observed in the deacylation of Hn-1CONHCH(CH2Ph)CO2C6H4NO2-p possessing long acyl chains (n 10-16) by comicelles of N-(N-dodecanoyl-L-histidyl)-L-leucine and (R)-(+)-N-α-methylbenzyl-NN-dimethyloctadecylammonium bromide.