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L-Phenylalanine is an aromatic organic compound containing amine and acid as functional groups. It is an essential amino acid and its structure can be considered as the derivative of 3-phenylpropionic acid, in which one hydrogen atom present at C-2 position is substituted with amino group. It is a chiral compound and consists of two optical isomers. It is also known as 2-amino-3-phenylpropanoic acid, beta-phenylalanine, L-alfa-amino-beta-phenylpropionic acid, H-Phe-OH and (S)-2-amino-3-phenylpropionic acid.
Other amino acids have been resolved by crystallization of their complexes with L-phenylalanine, and decomplexation with activated carbon: Chem. Lett., 113 (1984).
Formation of the N,N-dibenzyl benzyl ester by reaction with benzyl bromide and base, followed by LAH reduction and Swern oxidation, lead to the N,N-dibenzyl (S)-ɑ-amino aldehyde, a useful chiral intermediate: Org. Synth., 76, 110 (1998).
Hou, Y.; Hossain, G. S.; Li, J.; Shin, H. D.; Liu, L.; Du, G. Production of phenylpyruvic acid from L-phenylalanine using an L-amino acid deaminase from Proteus mirabilis: comparison of enzymatic and whole-cell biotransformation approaches. Appl. Microbiol. Biotechnol. 2015, 99 (20), 8391-8402.
Liu, S. P.; Liu, R. X.; Xiao, M. R.; Zhang, L.; Ding, Z. Y.; Gu, Z. H.; Shi, G. Y. A systems level engineered E. coli capable of efficiently producing L-phenylalanine. Process Biochem. 2014, 49 (5), 751-757.