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HomeProduct name listL-Homophe-OH

L-Homophe-OH

  • CAS NO.:943-73-7
  • Empirical Formula: C10H13NO2
  • Molecular Weight: 179.22
  • MDL number: MFCD00002619
  • EINECS: 213-403-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-29 17:54:30
L-Homophe-OH Structural

What is L-Homophe-OH?

Chemical properties

White Solid

What are the applications of 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].

The Uses of L-Homophe-OH

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.

The Uses of L-Homophe-OH

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.

Properties of L-Homophe-OH

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.
form  Solid
pka 2.32±0.10(Predicted)
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
CAS DataBase Reference 943-73-7(CAS DataBase Reference)

Safety information for L-Homophe-OH

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for L-Homophe-OH

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

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