L-Homophenylalanine

L-Homophenylalanine Basic information
Description References
Product Name:L-Homophenylalanine
Synonyms:(+)-2-Amino-4-phenylbutyric acid,98%;S)-α-Amino-benzenebutanoic acid;L-(S)-Homophenylalanine.HCl;L-Homophenylalanine ,98%;H-L-HPA-OH;Benzenebutanoicacid, a-aMino-, (aS)-;H-HoMophe-OH(HoMophenylalanine);RARECHEM BK PT 0049
CAS:943-73-7
MF:C10H13NO2
MW:179.22
EINECS:213-403-3
Product Categories:API intermediates;Homophenylalanine [Hph];Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Aromatics;Chiral Compounds;Phenylalanine analogs and other aromatic alpha amino acids;Chiral Compound;Amino Acids
Mol File:943-73-7.mol
L-Homophenylalanine Structure
L-Homophenylalanine 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.
pka2.32±0.10(Predicted)
form Solid
color White to Off-White
InChIKeyJTTHKOPSMAVJFE-VIFPVBQESA-N
CAS DataBase Reference943-73-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Safety Statements 22-24/25
WGK Germany 3
HS Code 29224999
MSDS Information
ProviderLanguage
(S)-alpha-Amino-benzenebutanoic acid English
ACROS English
SigmaAldrich English
L-Homophenylalanine Usage And Synthesis
DescriptionL-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.
ReferencesHwang, 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/

Chemical PropertiesWhite Solid
UsesAntitumor agent.
UsesL-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.
DefinitionChEBI: A non-proteinogenic L-alpha-amino acid that is an analogue of L-phenylalanine having a 2-phenylethyl rather than a benzyl side-chain.
Betaine 4-Phenylbutyric acid N-[(tert-Butoxy)carbonyl]-D-tryptophan 4-Aminobutyric acid Boc-D-Tyr-OH METHYL 4-(4-AMINOPHENYL)BUTANOATE Phenylacetone ALTRENOGEST Glycine L-Homophenylalanine FMOC-4-TRIFLUOROMETHYL-D-BETA-HOMOPHENYLALANINE (2S,3S)-2-Hydroxy-3-amino-4-phenylbutyric acid FMOC-PENTAFLUORO-D-BETA-HOMOPHENYLALANINE AMINO ACIDS L-BETA-HOMOPHENYLALANINE ALLYL ESTER HYDROCHLORIDE 2,4-DICHLORO-D-BETA-HOMOPHENYLALANINE HYDROCHLORIDE L(+)-Arginine 4-(4-Aminophenyl)butyric acid

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