L-Homophenylalanin

Bezeichnung:L-Homophenylalanin

CAS-Nr943-73-7

Englisch Name:L-Homophe-OH

CBNumberCB8206268

SummenformelC10H13NO2

Molgewicht179.22

MOL-Datei943-73-7.mol

Synonyma

L-Homophenylalanin

L-Homophenylalanin physikalisch-chemischer Eigenschaften

Schmelzpunkt	>300 °C(lit.)
alpha	45 º (C=1, 3N HCl 19 ºC)
Siedepunkt	311.75°C (rough estimate)
Dichte	1.1248 (rough estimate)
Brechungsindex	44 ° (C=1, 3mol/L HCl)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	Soluble in dilute aqueous acid.
Aggregatzustand	Solid
pka	2.32±0.10(Predicted)
Farbe	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 Datenbank	943-73-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	22-24/25
WGK Germany	3
HS Code	29224999

Gefahreninformationscode (GHS)

L-Homophe-OH Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
White Solid
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].
Verwenden
Antitumor agent.
Verwenden
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.
Vorbereitung Methode
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].
Einzelnachweise
[1] Ahmad A, et al. Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor. Biotechnology Advances, 2009; 27: 286-296.

L-Homophe-OH Upstream-Materialien And Downstream Produkte

L-Homophenylalanin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

943-73-7, L-Homophe-OH Verwandte Suche:

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