Phenylalanine

CAS Number 150-30-1
Molecular Formula C9H11NO2
Molecular Weight 165.192 g/mol
InChI Key COLNVLDHVKWLRT-UHFFFAOYSA-N
LogP -1.38
Synonyms
  • Phenylalanine
  • 150-30-1
  • (+/-)-3-Phenyl-2-aminopropanoic acid
  • (+/-)-Phenylalanine
  • (+/-)-beta-Phenyl-alpha-alanine
  • 2-Amino-3-phenylpropanoic acid
  • Alanine, phenyl-, DL-
  • Alanine, beta-phenyl-
  • DL-2-Amino-3-phenylpropionic acid
  • DL-3-Phenylalanine
  • DL-fenilalanina
  • DL-Phenylalanin
  • DL-Phenylalanine
  • DL-alpha-Amino-beta-phenylpropionic acid
  • DL-beta-Phenylalanine
  • DL-beta-Phenyl-alpha-alanine
  • NSC 9959
  • PHENYLALANINE, DL-
  • alpha-Aminohydrocinnamic acid, dl-
  • 2-Amino-3-phenylpropionic acid, dl-
  • EINECS 205-756-7
  • FEMA No. 3726
  • UNII-8P946UF12S
  • F
  • PHE
  • Phenylalanin
  • fenilalanina

Applications:


Amino Acids Analysis in Acid Gradient Condition



11 underivatized amino acids (aspartic acid, glutamic acid, alanine, valine, methionine, isoleucine, cysteine, phenylalanine, histidine, lysine, and arginine) are separated by a Primesep 100 HPLC column by reversed-phase and ion-exchange mechanisms with LC/MS compatible conditions without the use of ion-pair reagents. The HPLC separation uses a TFA (trifluoroacetic acid) gradient in a mobile phase of water acetonitrile (MeCN, ACN with evaporative light scattering detection (ELSD).



Application Analytes:

Alanine
Amino Acids
Arginine
Aspartic Acid
Cysteine
Glutamic Acid
Histidine
Isoleucine
Lysine
Methionine
Phenylalanine
Valine

Complex Mixture of Acids, Bases, Amino Acids, and Neutral Compounds



Primesep 100 separates a mixture of amino acids (tyrosine, phenylalanine), organic acids (benzoic acid, mandelic acid), amines (benzylamine, pyridine), and neutrals (benzonitrile, toluene) in one HPLC run by combining reversed-phase, cation-exchange, and polar interactions. The method is tunable and peak order can be changed significantly by adjusting acetonitrile and trifluoroacetic acid concentrations. The separation method uses a mobile phase mixture of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) and compatible with UV, mass spec (LC/MS) and evaporative light scattering (ELSD) detection.



Application Analytes:

Amino Acids
Benzoic Acid
Benzonitrile
Benzylamine
Mandelic Acid
Organic Acids
Phenylalanine
Pyridine
Toluene
Tyrosine

HPLC Analysis of the Catecholamine Pathway



Primesep 200 separates catecholamines in the catecholamine pathway in 10 minutes. Phenylalanine, tyrosine, DOPA, dopamine, norepinephrine, and epinephrine are baseline resolved by a combination of reversed-phase, ion-exchange, and ion-exclusion mechanisms. Excellent peak shape results with a mass spec compatible mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.



Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Phenylalanine
Tyrosine

Bufferless Ion Separation (BLIS™) Chromatography of Amino Acids (1)

Amino acids are the building blocks of proteins and are widely used as supplements.  Amino acids can exist in acidic, basic or zwitterionic form depending on the pH of their environment (mobile phase in this case).  Primesep 200 is a reverse-phase column with embedded weak acidic ion-pairing groups which allows for retention and separation of amino acids without requiring a buffer making it ideal for use with UV detection, mass spectrometry (MS), evaporative light scattering detection (ELSD).

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Phenylalanine
Tyrosine

HPLC Separation of Acidic, Basic and Zwitterionic Compounds on Special Columns for Retention of Polar Compounds


Primesep mixed-mode columns are designed to separate basic, acidic, neutral and zwitter-ionic compounds. Elution of these compounds is facilitated by acetonitrile and ions in the mobile phase. In all cases the retention time on mixed-mode columns is significantly longer than on traditional reverse-phase columns. Presence of cation-exchange mechanism in Primesep 100 column allows to achieve better retention and peak shape for analytes like phenylalanine and benzylamine. Various buffers can be used along with different detection techniques. This HPLC method can be adopted as a universal approach for analysis of basic, acidic and zwitter-ionic compounds in complex mixtures and formulations. Compounds can be monitored by UV, ELSD, CAD and LC/MS.



Application Analytes:

Benzoic Acid
Benzylamine
Phenylalanine
Zwitterion

HPLC Separation of Compounds of Catecholamine Pathway
The catecholamine neurotransmitters are amino-acid derivatives of tyrosine. DOPA, tyrosine, phenylalanine, norepinephrine, epinephrine, and dopamine and baseline are resolved on a Primesep 200 column with UV-transparent phosphate buffer. This method can be used for the analysis of catecholamines and related impurities in various matrices. The peak order and retention time can be changed by changing the amount of ACN, buffer concentration and buffer pH. Various buffers can be used to accommodate the desired detection technique. Primesep 200 is a reversed-phase cation-exchange mixed-mode column that can be used for analysis of polar neutral, polar ionizable, polar zwitterionic, hydrophobic neutral, and hydrophobic ionic compounds in the same run. Column can be operated in reverse-phase, cation-exchange, anion-exclusion, HILIC and mixed-modes depending on the mobile phase selection and the nature of the analytes. The column is compatible with LC/MS and does not require the use of ion-pairing reagents.

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Phenylalanine
Tyrosine

HPLC Separation of Amino Acids, Bases, Acids, and Neutrals on Obelisc R

Condition

Column Obelisc R, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 35/65%
Buffer AmAc 10 mM pH 4.0
Flow Rate 1.0 ml/min
Detection UV, 250 nm
 

Description

Class of Compounds Drug, Acid, Bases, Neutral, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

2,6-Lutidine
Benzoic Acid
Benzonitrile
Benzylamine
Phenol
Phenylalanine
Pyridine
Toluene
Tryptophan

Effect of both pH and Organic Content on a Separation of Sugars, Amino Acids, and Carboxylic Acids


In mixed-mode HILIC chromatography, selectivity of separation can be adjusted by amount of acetonitrile, amount of buffer and buffer pH. Buffer concentration and pH will affect retention of ionizable compounds to a different degree. Retention of neutral compounds can be adjusted by the amount of acetonitrile. Carboxylic acid, three amino acids and two sugars are separated by combination of HILIC and ion-exchange mechanisms. Compounds can be monitored by ELSD, Corona (CAD), LC/MS or low UV. UV-transparent mobile phase /buffer is required for UV monitoring of this mixed-mode separation. This HPLC method can be adopted as general approach for analysis of sugars, amino acids and carboxylic acids.



Application Analytes:

Aspartic Acid
Phenylalanine
Succinic Acid

HPLC Separation of Amino Acids on Obelisc R Column

Closely related compounds like amino acids can be separated on an Obelisc R column by various buffers depending on the amount of baseline separation required. By choosing different buffers, the separation between compounds can be adjusted based on application needs, especially those that require low organic concentration in the mobile phase. UV detection at 250nm.

Condition

Column Obelisc R, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 5/95%
Buffer AmFm
Flow Rate 1.0 ml/min
Detection UV, 250 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

3-Aminobenzoic Acid
Aspartame
Phenylalanine
Tryptophan

HPLC Separation of Phenylalanine, Glucosamine, and Tryptophan on Mixed-Mode Column

The Separation of Phenylalanine, Glucosamine and Tryptophan demonstrates how the small changes to the organic and/or buffer concentrations in the mobile phase affect the retention of compounds on a mixed-mode column by hydrophobic, ion-exchange and ion-exclusion mechanisms in reverse-phase HPLC chromatography. Evaporative Light Scattering Detector (ELSD) used 

Application Analytes:

Glucosamine
Phenylalanine
Tryptophan

HPLC Separation of Catecholamines on Primesep 100 Column with Phosphate Buffers

chr_284.gif

The catecholamine neurotransmitters are amino-acid derivatives of tyrosine. DOPA, tyrosine, phenylalanine, norepinephrine, epinephrine, and dopamine and baseline are resolved on a Primesep 100 column with UV-transparent phosphate buffer. This method can be used for analysis of catecholamines and related impurities in various matrices. Peak order and retention time can be changed by changing the amount of ACN, buffer concentration and buffer pH. Various buffers can be used to accommodate desired detection technique. Primesep 100 is a reversed-phase cation-exchange mixed-mode column that can be used for analysis of polar neutral, polar ionizable, polar zwitter-ionic, hydrophobic neutral, and hydrophobic ionic compounds in the same run. Column can be operated in reverse-phase, cation-exchange, anion-exclusion, HILIC and mixed-modes depending on the mobile phase selection and nature of analytes. Column is compatible with LC/MS and does not require use of ion-pairing reagents.



Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Epinephrine
Norepinephrine
Phenylalanine
Tyrosine

HPLC Separation of Amino Acids in Zero Organic Mode on Primesep 200 column

Essential and non-essential amino acids can be retained and separated in zero-organic mode on Primesep mixed-mode HPLC columns. Zero-organic mode is required to monitor isotopes of carbon. Amino acids are retained by combination of reversed-phase and cation-exchange mechanisms. At lower pH, some of the amino acids are more hydrophobic. Buffer pH will affect ionization state of amino acids, and at higher pH (above 2.5), the amino acids will be less hydrophobic and retentive in zero-organic mode. Amino acids can be monitored by low UV. Method can be used in archeological research for analysis of various molecules where presence of organic component of the mobile phase interferes with analysis.



Application Analytes:

Histidine
Isoleucine
Leucine
Lysine
Phenylalanine
Tyrosine
Valine

HPLC Separation of Amino Acids in HILIC and Cation-Exchange Modes

chr_306.gif

Amino acids can be retained and separated on a Primesep S2 column in HILIC/cation-exchange mode.



Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Phenylalanine
Tyrosine

HPLC Separation of Lysine and Arginine from Other Amino Acids

 

Application Notes: Amino acids are polar ionic compounds which are not retained on reversed-phase column without ion-pairing reagent. In our application, lysine and arginine can be separated from other amino acids. Amino acids with a pH between 3 and 5 and with one basic and one acidic group become very polar. Therefore these amino acids don’t have strong ion-exchange interaction with Primesep C stationary phase. Amino acids with two amino groups still carry positive net charge and can interact with stationary phase by cations-exchange mechanism. pH variation of the mobile phase can be an effective tool to adjust selectivity of separation for zwitter-ionic, basic and acidic compounds. This method can be used for separation of mono-charged compounds from compounds having an extra charge.

Application Columns: Primesep C
Application compounds: Aspartic acid, Glutamic acid, Aspargine, Glycine, Proline, Alanine, Phenylalanine, Tyrosine, Leucine, Lysine, Arginine
Detection technique: UV, LC/MS, ELSD/CAD



Application Analytes:

Alanine
Arginine
Asparagine
Aspartic Acid
Glutamic Acid
Glycine
Leucine
Lysine
Phenylalanine
Proline
Tyrosine

HPLC Separation of Mixture of Essential Amino Acids on Primesep 100 Column
 

Condition

Column Primesep 100, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 20/80%
Buffer Gradient H2SO4 0.05-0.2% 25 min
Flow Rate 1.0 ml/min
Detection UV, 200 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

Amino Acids
D-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Histidine hydrochloride monohydrate
L-Isoleucine
L-Methionine
Methionine
Phenylalanine
Tryptophan
Valine

HPLC Separation of Mixture of 12 Amino Acids on Primesep 100 Column
 

Condition

Column Primesep 100, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 35/65%
Buffer H2SO4 0.05% 12 min hold, gradient 0.05-0.20, 13 min
Flow Rate 1.0 ml/min
Detection UV, 200 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

Amino Acids
Arginine
Asparagine
Cysteine
D-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Cysteine
L-Methionine
Leucine
Methionine
Phenylalanine
Proline
Tryptophan
Valine