Tyrosine

CAS Number	60-18-4
Molecular Formula	C9H11NO3
Molecular Weight	181.191 g/mol
InChI Key	OUYCCCASQSFEME-QMMMGPOBSA-N
LogP	-2.3
Synonyms	L-tyrosine tyrosine 60-18-4 (S)-Tyrosine p-Tyrosine H-Tyr-OH L-p-Tyrosine (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid 4-Hydroxy-L-phenylalanine L-(-)-Tyrosine Tyrosine, L- Tyrosinum [Latin] Tyrosine (VAN) Tirosina [Spanish] (-)-alpha-Amino-p-hydroxyhydrocinnamic acid (S)-alpha-Amino-4-hydroxybenzenepropanoic acid 3-(4-Hydroxyphenyl)-L-alanine L-Phenylalanine, 4-hydroxy- beta-(p-Hydroxyphenyl)alanine Tyrosinum (S)-3-(p-Hydroxyphenyl)alanine L-Tyrosin (S)-(-)-Tyrosine Tyrosine [USAN:INN] L-2-Amino-3-p-hydroxyphenylpropanoic acid FEMA No. 3736 Rxosine L-Tyrosine, homopolymer Tyrosine Power (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid HSDB 2003 alpha-Amino-beta-(4-hydroxyphenyl)propionic acid AI3-09055 tirosina Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)- NSC 82624 alpha-Amino-p-hydroxyhydrocinnamic acid, (-)- L-Tyr (S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid L-Tyrosine, monomer tyr alpha-Amino-4-hydroxybenzenepropanoic acid, (S)- Free-Form L-Tyrosine UNII-42HK56048U L-Tyrosine (9CI) Benzenepropanoic acid, alpha-amino-4-hydroxy-, (S)- Tyrosine (USP/INN) 4ts1 EINECS 200-460-4 beta-p-Hydroxyphenylalanine 2-Amino-3-(4-hydroxyphenyl)propanoic acid, (S)- CHEBI:17895 OUYCCCASQSFEME-QMMMGPOBSA-N 3-(p-Hydroxyphenyl)alanine MFCD00002606 55520-40-6 NCGC00159350-02 Tyrosine (L-Tyrosine) DSSTox_CID_3730 Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs L-2-Amino-3-(4-hydroxyphenyl)propionic acid DSSTox_RID_77170 DSSTox_GSID_23730 2-Amino-3-(p-hydroxyphenyl)propionic acid DD69927C-C6A8-4BC6-8E9A-0AB423B176E7 CAS-60-18-4 Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs, oxidized with hydrogen peroxide Melanin synthesized from Tyr substrate catalyzed by tyrosinase for 6 hrs, oxidized with hydrogen peroxide, <3 kd fraction Melanin synthesized from Tyr substrate catalyzed by tyrosinase, brominated with N-bromosuccinimide Melanin synthesized from Tyr substrate catalyzed by tyrosinase, sulfonated using sulfur trioxide/DMF complex for 1.5-7 hours DTY Benzenepropanoate 2csm (L)-Tyrosine (-) tyrosine H-Tyr L-Tyrosine (JAN) (-)-.alpha.-Amino-p-hydroxyhydrocinnamic acid L-Tyrosine;H-Tyr-OH

Applications:

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.

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.

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).

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

HPLC Analysis of Polar Basic and Acetic Compounds on Primesep AB Column

Mixture of polar acidic and basic compounds is separated on a Primesep AB mixed-mode HPLC column. Dopamine and tyrosine are retained by combination of reversed-phase and cation-exchange mechanisms. Maleic acid is retained by anion-exchange mechanism, and benzoic acid is retained by reversed-phase mechanism. Primesep AB is a trimodal column with a C12 hydrophobic chain and cation-exchange and anion exchange groups on the surface. Method utilizes UV detection but can be used with other detection techniques (ELSD, LC/MS, Corona).

Benzoic Acid
Dopamine
Maleic Acid
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.

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

HPLC Separation of Catecholamines on Primesep 100 Column with Phosphate Buffers

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.

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.

Histidine
Isoleucine
Leucine
Lysine
Phenylalanine
Tyrosine
Valine

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

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

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

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

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

Condition
Column	Primesep 100, 4.6x250 mm, 5 µm, 100A
Mobile Phase	MeCN/H2O - 35/75%
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

Amino Acids
Arginine
Cysteine
Glycine
L-Cysteine
L-Glutamine
Proline
Tyrosine