Description
L-Homophenylalanine is an amino acid derivative. It has been extensively used in the pharmaceutical industry as a precursor for production of angiotensin-converting enzyme (ACE) inhibitor: enalapril, delapril, quinapril and ramipril, which possesses significant clinical application in the management of hypertension and congestive heart failure (CHF). It acts as an anti-tumor reagent.
References
Hwang, J. Y., et al. "Simultaneous synthesis of 2-phenylethanol and L-homophenylalanine using aromatic transaminase with yeast Ehrlich pathway." Biotechnology & Bioengineering 102.5(2009):1323-9.
Ahmad, A. L., P. C. Oh, and S. R. Abd Shukor. "Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor."Biotechnology Advances 27.3(2009):286-296.
https://www.alfa.com/en/catalog/H27295/
Application
L-homophenylalanine is used almost exclusively as single stereoisomer in pharmaceutical drug production. L-homophenylalanine as a common building block, due to the presence of L-homophenylalanine moiety as the central pharmacophore unit. L-homophenylalanine is also an important chiral intermediate to synthesize a variety of novel pharmaceuticals including β-lactam antibiotics, acetylcholinesterase inhibitor and neutral endopeptidace (NEP) inhibitor which retained their status as major contributors to human health preservation. L-homophenylalanine acts as a precursor for the synthesis of NEP inhibitors, which complements the effects of ACE inhibitors when used simultaneously, potentiates the outcome in the management of hypertension and congestive heart failure[1].
Chemical Properties
White Solid
Uses
L-Homophenylalanine is used as a precursor in the pharmaceutical industry for the production of angiotensin-converting enzyme (ACE) and R-(-)-Homophenylalanin-ethylester. It is also involved in the synthesis of NEPA [(S,S)-N-(1-Ethoxycarbonyl-3-phenylpropyl)alanine], which is a key intermediate to prepare the ACE-inhibitors: enalapril, delapril, quinapril and ramipril. It acts as an anti-tumor reagent.
Definition
ChEBI: A non-proteinogenic L-alpha-amino acid that is an analogue of L-phenylalanine having a 2-phenylethyl rather than a benzyl side-chain.
Production Methods
Asymmetric reduction of prochiral ketone remains one of the most investigated methods to date for production of chiral L-homophenylalanine. One of the most established method for synthesizing L-homophenylalanine on a laboratory scale was carried out via enzyme-catalyzed asymmetric synthesis of keto acids. In this method, prochiral ketone was converted via reductive amination to enantiopure products with bulky side chains by addition of biocatalysts such as L-homophenylalanine dehydrogena. in the presence of cofactor. L-phenylalanine dehydrogenase is by and large preferred as it has mainly a catabolic function and accepts a wide variety of keto acids as substrates hence it is generally employed in the synthesis of L-homophenylalanine which carries very bulky side chains[1].
References
[1] Ahmad A, et al. Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor. Biotechnology Advances, 2009; 27: 286-296.
