15099-85-1

Basic information

• Product Name: L-PHENYLALANINE
• Synonyms: ALPHA-AMINO-BETA-PHENYL PROPIONIC ACID;beta-Homophenylalanine;3-Amino-4-phenylbutyric acid;3-azanyl-4-phenyl-butanoic acid;DL-beta-Homophenylalanine >=98.0% (HPLC);beta-Aminobenzenebutanoic acid;PHENYALANINE, L-;PHENYLALANINE
• CAS NO: 15099-85-1
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 200-568-1
• Mol File: 15099-85-1.mol

Chemical Properties

• Melting Point: 270-275 °C (dec.)(lit.)
• Boiling Point: 329.5 °C at 760 mmHg
• Flash Point: 153.1 °C
• Appearance: /powder
• Density: 1.164
• Storage Temp.: 2-8°C(protect from light)
• Solubility: H2O: 0.1 M at 20 °C, clear, colorless
• PKA: 2.2(at 25℃)
• BRN: 2938025
• CAS DataBase Reference: L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-PHENYLALANINE(15099-85-1)
• EPA Substance Registry System: L-PHENYLALANINE(15099-85-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: AY7535000
• F: 10
• Hazardous Substances Data: 15099-85-1(Hazardous Substances Data)

Usage

Safety Profile

Mildly toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

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

Upstream product

• 26250-86-2 (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid 
• 100-39-0 benzyl bromide 
• 5130-24-5 Vinyl chloroformate 
• 153708-38-4 (S,S)-6-benzyl-2-tert-butyl-1,3-dimethyl-4-pyrimidinone 
• 159025-89-5 3-[(t-butoxycarbonyl)amino]-4-phenylbutanenitrile 
• 777885-07-1 (+/-)-4-benzyl-2-azetidinone 
• 67-56-1 methanol 
• 193954-28-8 (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoic acid 
• 51871-62-6 (S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid 
• 211618-76-7 (S)-4-benzyl-2-azetidinone 
• 1039025-18-7 N-[(1S)-1-cyanomethyl-2-phenylethyl]-2,4,6-trimethylbenzenesulfonamide 
• 97206-05-8 methyl N-(benzyloxycarbonyl)-(3S)-3-amino-4-phenylbutanoate 
• 153708-33-9 (S)-6-benzyl-2-tert-butyl-1-methoxymethyl-3-methyl-2,3-dihydro-4(1H)-pyrimidinone 
• 100-52-7 benzaldehyde 

Downstream Products

• 78175-24-3 (S)-3-(2,4-Dinitro-phenylamino)-4-phenyl-butyric acid 
• 211618-76-7 (S)-4-benzyl-2-azetidinone 
• 26250-86-2 (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid 
• 211619-01-1 (2S,3R)-2-Benzyl-3-methyl-4-oxo-azetidine-1-carboxylic acid (pyridin-4-ylmethyl)-amide 
• 211619-02-2 (2S,3S)-2-Benzyl-3-methyl-4-oxo-azetidine-1-carboxylic acid (pyridin-4-ylmethyl)-amide 
• 211618-81-4 (3R,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one 
• 211618-79-0 (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one 
• 211618-80-3 4(S)-benzyl-3(S)-methylazetidin-2-one 

Relevant articles and documents

METHOD FOR OBTAINING OPTICALLY PURE AMINO ACIDS

This invention relates to a method for obtaining optically pure amino acids, including optical resolution and optical conversion. This method significantly shortens the time taken for optical transformation, and enables the repeated use of an organic solution containing a enantioselective receptor, to thereby obtain optically pure amino acids in a simple and remarkably efficient manner, and to enable the very economical mass production of optically pure amino acids.

Thermal cleavage of the Fmoc protection group

The Fmoc protection group is among the most commonly used protection groups for the amino function. A fast method for the thermal deavage of this protection group under base-free conditions without the need for dibenzofulvene scavengers is presented. The advantages of this method include straightforward testability by means of a simple high-temperature NMR experiment, usually high yields, and good selectivity towards the BOC protection group and t-butyl ethers.

HETEROCYCLIC MODULATORS OF PKB

The invention relates to heterocyclic compounds of Formula I and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein Formula (I). The invention also relates to the therapeutic use of such compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis

The work describes fluorine-activated and N-Boc-activated β-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the β-lactam ring causes the ring to open in high enantioselectivity

Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents

Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala- β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.

Candida antarctica lipase B-catalyzed ring opening of 4-arylalkyl-substituted β-lactams

The Lipolase-catalyzed ring opening of racemic 4-benzyl- 3 and 4-phenylethyl-2-azetidinone 4 was performed with 0.5 equiv of H2O in diisopropyl ether at 45 °C. The resulting (S)-β-amino acid 5 or 6 (ee ≥ 87%) and (R)-β-lactam 7 or 8 (ee >99%) enantiomers could easily be separated. The ring opening of enantiomeric β-lactams with 18% aqueous HCl afforded the corresponding enantiopure β-amino acid hydrochlorides 9 and 10 (ee >99%).

Lipase-involved strategy to the enantiomers of 4-benzyl-β-lactam as a key intermediate in the preparation of β-phenylalanine derivatives

A simple chemoenzymatic method for the preparation of the enantiomers of 4-benzyl-β-lactam (4-benzylazetidin-2-one) from allylbenzene has been described. The enantiomers of this key intermediate have been used to produce the corresponding enantiomers of β-phenylalanine and N-Boc-protected β-phenylalanine amide through the simple cleavage of the lactam ring by acid-catalyzed hydrolysis and by ammonolysis, respectively. Burkholderia cepacia lipase-catalyzed kinetic double resolution techniques were responsible for achieving enantiopurity in the products. This was performed through the acylation of N-hydroxymethylated β-lactam followed by the butanolysis of the obtained (S)-ester. Direct lipase-catalyzed cleavage of the β-lactam ring has also been studied.

Novel compounds that inhibit dipeptidyl peptidase (DPP-IV) and neprilysin (NEP) and/or angiotensin converting enzyme (ACE)

This invention relates to novel compounds, compositions containing the compounds, that inhibit dipeptidyl peptidase (especially DPP-IV) and neprilysin (NEP, neutral endopeptidase) as well as dipeptidyl peptidase (especially DPP-IV) and angiotensin converting enzyme (ACE) and/or dipeptidyl Peptidase (especially DPP-IV) and vasopeptidases (especially ACE and NEP). These compounds and pharmaceutical compositions thereof are useful for the treatment as well as the prevention of type 2 diabetes mellitus.

Azetidinone derivatives for the treatment of HCMV infections

A compound of formula I wherein R1is hydrogen, methyl, ethyl, methoxy or methylthio; R2and R3each independently is hydrogen or lower alkyl; R4is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6wherein m is the integer 1 or 2 and R6is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4and R5together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7wherein R7is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2and R3each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.

β-Casomorphins: Substitution of phenylalanine with β-homo phenylalanine increases the μ-type opioid receptor affinity

Two analogues of bovine β-casomorphin-7 and β-casomorphin-5 containing a β-homo phenylalanine in substitution of the phenylalanine in position 3 were synthesised and tested for their μ-opioid receptor affinity. The modification enhanced the μ receptor affinity 5-fold in the case of modified β-CM-7 and 2-fold for modified β-CM-5 when compared to the natural peptides. (C) 2000 Elsevier Science Ltd. All rights reserved.