331955-24-9

Basic information

• Product Name: Phenylalanine, 2-chloro-N-[(phenylmethoxy)carbonyl]-
• Synonyms: 2-Benzyloxycarbonylamino-3-(2-chloro-phenyl)-propionic acid
• CAS NO: 331955-24-9
• Molecular Formula: C17H16ClNO4
• Molecular Weight: 333.76600
• Mol File: 331955-24-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 124 - 125 °C
• CAS DataBase Reference: Phenylalanine, 2-chloro-N-[(phenylmethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylalanine, 2-chloro-N-[(phenylmethoxy)carbonyl]-(331955-24-9)
• EPA Substance Registry System: Phenylalanine, 2-chloro-N-[(phenylmethoxy)carbonyl]-(331955-24-9)

Safety Data

• Hazardous Substances Data: 331955-24-9(Hazardous Substances Data)

Upstream product

• 14091-11-3 rac-2-chlorophenylalanine 
• 501-53-1 benzyl chloroformate 
• 10466-61-2 (2S)-amino-4-methylpentanamide hydrochloride 
• 203640-54-4 Z-(RS)-Phe(2Cl)-O-carbamoylmethyl 
• 169676-25-9 Z-DL-Phe(2Cl)-OCH₂CF₃ 

Downstream Products

• 141971-12-2 Z-DL-Phe(2Cl)OMe 
• 169676-25-9 Z-DL-Phe(2Cl)-OCH₂CF₃ 

Relevant articles and documents

Superiority of the carbamoylmethyl ester as an acyl donor for the kinetically controlled amide-bond formation mediated by α-chymotrypsin

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalysed kinetically controlled peptide-bond formation is demonstrated in the couplings of an inherently poor amino acid substrate, Ala, with various amino acid residues as amino components and in the couplings of non-protein amino acids such as halogenophenylalanines as carboxylic components. Furthermore, this approach is applied to the amide-bond formation between an amino acid residue and a chiral amine, which is highly diastereoselective.

Remarkable effects of donor esters on the α-chymotrypsin-catalyzed couplings of inherently poor amino acid substrates

The extremely low efficiency during the α-chymotrypsin-catalyzed coupling of an inherently poor amino acid substrate, e.g., alanine, using the methyl ester as an acyl donor was significantly improved using esters such as the 2,2,2-trifluoroethyl or carbamoylmethyl ester. The ameliorating effect of the latter ester was especially significant.