L-Homophe-OH Chemical Properties

Melting point:

>300 °C(lit.)

alpha 

45 º (C=1, 3N HCl 19 ºC)

Boiling point:

311.75°C (rough estimate)

Density 

1.1248 (rough estimate)

refractive index 

44 ° (C=1, 3mol/L HCl)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in dilute aqueous acid.

pka

2.32±0.10(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1/C10H13NO2/c11-9(10(12)13)7-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/s3

InChIKey

JTTHKOPSMAVJFE-VIFPVBQESA-N

SMILES

C(O)(=O)[C@H](CCC1=CC=CC=C1)N |&1:3,r|

CAS DataBase Reference

943-73-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:(S)-alpha-Amino-benzenebutanoic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

L-Homophe-OH Usage And Synthesis

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.

Uses

Antitumor agent.

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.

L-Homophe-OH(943-73-7)Related Product Information

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• Boc-D-Tyr-OH
• ALTRENOGEST
• α-Lipoic Acid
• L(+)-Arginine
• Glycine
• Betaine
• 4-Phenylbutyric acid
• METHYL 4-(4-AMINOPHENYL)BUTANOATE
• 4-Aminobutyric acid
• L-Homophenylalanine ethyl ester hydrochloride
• Phenylacetone
• N-[(tert-Butoxy)carbonyl]-D-tryptophan
• FMOC-4-TRIFLUOROMETHYL-D-BETA-HOMOPHENYLALANINE
• BOC-(S)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID
• [-/+]-2-AMINO-4-PHENYLBUTYRIC ACID,DL-ALPHA-AMINO-4-PHENYLBUTYRIC ACID
• 2,4-DICHLORO-L-BETA-HOMOPHENYLALANINE HYDROCHLORIDE
• N-T-BUTOXYCARBONYL-(S)-3-AMINO-4-PHENYLBUTYRIC ACID,(S)-3-(BOC-AMINO)-4-PHENYLBUTYRIC ACID