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

CAS Number 59-92-7
Molecular Formula C9H11NO4
Molecular Weight 197.190 g/mol
InChI Key WTDRDQBEARUVNC-LURJTMIESA-N
LogP -2.39
Synonyms
  • L-Dopa
  • 3-Hydroxy-L-tyrosine
  • L-Tyrosine, 3-hydroxy-
  • 59-92-7
  • Levodopa
  • L-Tyrosine, 3-hydroxy-
  • (-)-3,4-Dihydroxyphenylalanine
  • (-)-Dopa
  • (2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
  • 3-(3,4-Dihydroxyphenyl)-L-alanine
  • 3,4-Dihydroxy-L-phenylalanine
  • 3,4-Dihydroxyphenyl-L-alanine
  • 3-Hydroxy-L-tyrosine
  • Alanine, 3-(3,4-dihydroxyphenyl)-, L-
  • Alphadopa
  • Bendopa
  • Cidandopa
  • Deadopa
  • Dihydroxy-L-phenylalanine
  • DOPA, L-
  • Dopaflex
  • Dopaidan
  • Dopalina
  • Doparkine
  • Dopasol
  • Dopaston
  • Dopaston SE
  • Dopastone
  • Dopastral
  • Dopicar
  • Eldopal
  • Eldopar
  • Eldopatec
  • Eurodopa
  • Helfo-dopa
  • Insulamina
  • L-(-)-Dopa
  • L-3-(3,4-Dihydroxyphenyl)alanine
  • L-4,5-Dihydroxyphenylalanine
  • Laradopa
  • Larodopa
  • L-β-(3,4-Dihydroxyphenyl)-α-alanine
  • Maipedopa
  • Pardopa
  • Syndopa
  • Veldopa
  • Weldopa
  • β-(3,4-Dihydroxyphenyl)alanine
  • β-(3,4-Dihydroxyphenyl)-L-alanine
  • β-(3,4-Dihydroxyphenyl)-α-L-alanine
  • Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-
  • Biodopa
  • Brocadopa
  • Cerepap
  • L-(o-Dihydroxyphenyl)alanine
  • L-O-Dihydroxyphenylalanine
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
  • beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  • beta-(3,4-Dihydroxyphenyl)-L-alanine
  • 3,4-Dihydroxyphenylalanine
  • Dopal-fher
  • EINECS 200-445-2
  • Helfo DOPA
  • L-o-Hydroxytyrosine
  • NSC 118381
  • Sobiodopa
  • Levodopum
  • UNII-46627O600J
  • (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
  • (2S)-2-amino-3-(3,4-dihydroxyphenyl)propionic acid
  • Dihydroxyphenylalanine
  • Dopal
  • Dopar
  • Doparl
  • Doprin
  • L-3-(3,4-Dihydroxyphenyl)-Alanine
  • L-4-5-Dihydroxyphenylalanine
  • L-Dihydroxyphenylalanine
  • L-b-(3,4-Dihydroxyphenyl)-a-alanine
  • L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  • Ledopa
  • Levedopa
  • Levopa
  • Parda
  • Prodopa
  • b-(3,4-Dihydroxyphenyl)-L-alanine
  • b-(3,4-Dihydroxyphenyl)-a-L-alanine
  • b-(3,4-Dihydroxyphenyl)alanine
  • beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
  • beta-(3,4-dihydroxyphenyl)-L-alanine
  • beta-(3,4-dihydroxyphenyl)alanine
  • (2S)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate
  • L-dopa zwitterion
  • 23734-74-9
  • 25525-15-9
  • 34241-25-3
  • 72572-99-7
  • 72573-00-3
  • 88250-23-1
  • 90638-38-3

Applications:


HPLC Separation of Neurotransmitters
The neurotransmitters dl-DOPA, creatinine, hydroxytryptophan (5-HTP), and serotonin are separated in less than 4 minutes on a short 50 mm Primesep 200 column. The HPLC separation uses a mobile phase of water, acetonitrile (MeCN, ACN) and trifluoroacetic acid (TFA) and UV detection at 250 nm. Ion-pair reagents were not needed for retention of these polar, hydrophilic compounds, instead, a combination of ion-exchange and reversed-phase interactions were used.

Condition

Column Primesep 200, 4.6x50 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 80/20%
Buffer TFA - 0.05%
Flow Rate 1.0 ml/min
Detection UV, 250 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds dl-DOPA, Creatinine, Hydroxytryptophan (5-HTP), Serotonin
 

Application Analytes:

Creatinine
DOPA (3,4-dihydroxy-L-phenylalanine)
Hydroxytryptophan
Serotonin

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.

Condition

Column Primesep 200, 3.2x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA
Flow Rate 0.5 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

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 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.

Condition

Column Primesep 200, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA, AmFm
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

Application Analytes:

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

HPLC Separation of Polar and Hydrophobic Drugs on Obelisc R and N

Condition

Column Obelisc N, Obelisc R 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer H3PO4
Flow Rate 1.0 ml/min
Detection UV, 220 nm
 

Description

Class of Compounds Drug, Acid, Preservative,  Hydrophilic, Ionizable, Hormone
Analyzing Compounds Propyl paraben,  Dopamine, DOPA
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
Dopamine
Propylparaben

Separation of Serotonin, Dopamine, and Related Compounds
Catecholamines are chemical compounds derived from the amino acid tyrosine containing catechol and amine groups. Some of them are biogenic amines. Retention of compounds of the catecholamine pathway is achieved on Obelisc N column. All polar compounds are well retained by combination of HILIC and ion-exchange mechanisms. Obelisc N columns produce very good peak shapes for all analytes. The method is very sensitive to amount of ACN, buffer and buffer pH. The retention time changes with variation of the main parameters. This method can be used for quantitation of biogenic amines and related compounds (homovanillic acid, dihydroxyphenyl acetic acid, serotonin, dopamine, epinephrine, hydroxytryptophan, epinephrine and DOPA) in urine, blood and other biological fluids. Further optimization of this HPLC method can be used during screening and validation. Amines and acids can be analyzed in the same run and retained by a combination of polar organic mode, cation-exchange and anion-exchange modes. Various buffers within specified pH can be employed (ammonium formate, ammonium acetate, sodium phosphate, etc.).

Condition

Column Obelisc N, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmAc pH 4.0- 30 mM
Flow Rate 1.0 ml/min
Detection UV, 270 nm
 

Description

Class of Compounds Drug, Acid, Monocarboxylic acid,  Hydrophilic, Ionizable, Hormone
Analyzing Compounds Homovanillic acid, Dihydroxyphenyl acetic acid, Serotonin, Dopamine, Epinephrine, Hydroxytryptophan, DOPA
 

Application Analytes:

DOPA (3,4-dihydroxy-L-phenylalanine)
DOPAC (Dihydroxyphenylacetic Acid)
Dopamine
Epinephrine
Homovanillic Acid
Hydroxytryptophan
Norepinephrine
Serotonin

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.

Condition

Column Primesep 100, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer Na2HPO4
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Tyrosine, DOPA, Phenylalanine, Norepinephrine, Epinephrine, Dopamine
 

Application Analytes:

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

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.

Condition

Column Primesep S2, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmFm
Flow Rate 1.0 ml/min
Detection UV, 270 nm
 

Description

Class of Compounds Drug, Acid, Monocarboxylic acid,  Hydrophilic, Ionizable, Hormone
Analyzing Compounds Dopa, Tyrosine, Phenylalanine
 

Application Analytes:

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

Generic Screening Method for Complex Mixtures

Condition

Column Primesep 200, 4.6*150 mm 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer H2SO4
Flow Rate 1.0 ml/min
Detection UV, 215 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Hormone
Analyzing Compounds Uracil, Epinephrine, DOPA, 2,6-Lutidine, Benzylamine, Hydroxytrypthophan, Homovanillic acid, Phenol, Tryptophan , 2,3-DHBA, Benzoic acid, Methylparaben, Ethylparaben, Toluene, Amitriptyline
 

Application Analytes:

2,3-Dihydroxybenzoic Acid
2,6-Lutidine
Amitriptyline
Benzoic Acid
Benzylamine
DOPA (3,4-dihydroxy-L-phenylalanine)
Epinephrine
Ethyl Paraben
Homovanillic Acid
Hydroxytryptophan
Methylparaben
Phenol
Toluene
Tryptophan
Uracil