| CAS Number | 54-12-6 |
|---|---|
| Molecular Formula | C11H12N2O2 |
| Molecular Weight | 204.230 |
| InChI Key | QIVBCDIJIAJPQS-UHFFFAOYSA-N |
| LogP | -1.05 |
| Synonyms |
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Applications:
HPLC Method for Separation of a Mixture of Tryptophan and its Catabolites on Primesep 100 Column
October 3, 2023
High Performance Liquid Chromatography (HPLC) Method for Analysis of Mixture of Tryptophan and its Catabolites on Primesep 100 by SIELC Technologies
Separation type: Liquid Chromatography Mixed-mode
Tryptophan and its catabolites participate in several biological pathways, having roles in protein synthesis, serving as precursors to bioactive molecules, and influencing several physiological processes. Here’s an overview considering a mixture of tryptophan and its catabolites:
Tryptophan:
- Essential Amino Acid: Tryptophan is a precursor to several important compounds, including serotonin and melatonin.
- In Protein Synthesis: Incorporated into proteins during protein synthesis.
Catabolites:
1. Serotonin:
- Neurotransmitter: Regulates mood, appetite, and sleep, among other functions.
- Derivative: Melatonin, which regulates the sleep-wake cycle.
2. Kynurenine Pathway (Major catabolic pathway of tryptophan):
- Kynurenine: An intermediate and precursor to several bioactive compounds.
- Kynurenic Acid: An NMDA receptor antagonist, believed to have neuroprotective effects.
- Xanthurenic Acid: Its physiological roles are still being explored, but it’s often studied for its relation to diabetes and neurological conditions.
- 3-Hydroxykynurenine: Can generate reactive oxygen species, potentially contributing to cellular stress.
- Quinolinic Acid: A neuroactive metabolite that can act as an NMDA receptor agonist.
3. Indoleamine 2,3-dioxygenase (IDO) Pathway:
- Tryptophan can be degraded into several catabolites via the IDO pathway, influencing immune response and cell proliferation.
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Tryptophan and its Catabolites can be retained, separated and analyzed on a Primesep 100 mixed-mode stationary phase column using an gradient analytical method with a simple mobile phase of water, Acetonitrile (MeCN), and a sulfuric acid as a buffer. This analysis method can be detected using UV at 220 nm.
High Performance Liquid Chromatography (HPLC) Method for Analyses of Mixture of Tryptophan and its Catabolites
Condition
| Column | Primesep 100, 4.6 x 150 mm, 5 µm, 100 A, dual ended |
| Mobile Phase | Gradient MeCN 5-50% in 10 min, with 2 min hold afterwards |
| Buffer | Gradient H2SO4 from 0.1-0.2% in 10 min, with 2 min hold afterwards |
| Flow Rate | 1.0 ml/min |
| Detection | UV 220 nm |
Description
| Class of Compounds | Essential Amino Acid Tryptophan and its Catabolites |
| Analyzing Compounds | Tryptophan, Picolinic Acid, Kynurenine, 3-Hydroxykynurenine, 3-Hydroxyanthranilic acid |
Application Column
Primesep 100
Column Diameter: 4.6 mm
Column Length: 150 mm
Particle Size: 5 µm
Pore Size: 100 A
Column options: dual ended
3-Hydroxykynurenine
Kynurenine
Picolinic Acid
Tryptophan
HPLC Separation of Mixture of Nine Essential Amino acids and Arginine on Newcrom AH Column
September 25, 2020
Essential amino acids cannot be made by the body. As a result, they must come from food.
The 9 essential amino acids are: histidine, isoleucine, leucine, lysine, methionine, phenylalanine, threonine, tryptophan, and valine.
| Column | Newcrom AH, 4.6×150 mm, 5 µm, 100A |
| Mobile Phase | MeCN – 5% |
| Buffer | Gradient Formic Acid – 3-9%, 20 min |
| Flow Rate | 1.0 ml/min |
| Detection | CAD |
| Class of Compounds |
Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | L-Threonine (Thr/T), L-Valine (Val/V), DL-Methionine (Met/M), L-Isoleucine (Ile/I), L-Leucine (Leu/L), L-Phenylalanine (Phe/F), L-Histidine (His/H), Lysine (Lys/K) , L- Tryptophan (Trp/W), L-Arginine (Arg/R) |
Application Column
Newcrom AH
The Newcrom columns are a family of reverse-phase-based columns. Newcrom A, AH, B, and BH are all mixed-mode columns with either positive or negative ion-pairing groups attached to either short (25 Å) or long (100 Å) ligand chains. Newcrom R1 is a special reverse-phase column with low silanol activity.
Select optionsHistidine
Isoleucine
L-Threonine
Leucine
Lysine
Methionine
Phenylalanine
Tryptophan
Valine
HPLC Separation of Biogenic Amines on Primesep 100 Column
April 30, 2020
Tryptophan is an essential amino acid used in the synthesis of proteins. Tryptamine is structurally similar to tryptophan. Serotonin is a neurotransmitter derived from tryptophan. Dimethyltryptamine and 5-MeO-DMT are psychedelic substances derived from tryptamine. All the compounds have similar structures and can present difficulties to separation in reverse-phase HPLC. They can be separated using the Primesep 100 mixed-mode column in gradient analysis with acetonitrile (ACN) and water mobile phase with ammonium formate (AmFm) buffer, making the method MS-compatible. The amines can also be UV detected at 280nm.
| Column | Primesep 100, 4.6×150 mm, 5 µm, 100A |
| Mobile Phase | Gradient MeCN – 40-50%, 15 min |
| Buffer | Gradient AmFm pH 3.0- 20-80 mM, 15 min |
| Flow Rate | 1.0 ml/min |
| Detection | UV 280 nm, MS-compatible mobile phase |
| Class of Compounds |
Drug, Hydrophilic, Supplements, Monoamine, Neurotransmitter |
| Analyzing Compounds | Serotonin, Tryptophan, N,N-dimethyltryptophan, N,N-Dimethyl-5-methoxytryptamine, Tryptamine, N,N-dimethyltryptamine |
Application Column
Primesep 100
The Primesep family of mixed-mode columns offers a wide variety of stationary phases, boasting unprecedented selectivity in the separation of a broad array of chemical compounds across multiple applications. Corresponding Primesep guard columns, available with all stationary phases, do not require holders. SIELC provides a method development service available to all customers. Inquire about our specially-tailored custom LC-phases for specific separations.
Select optionsN,N-Dimethyltryptamine
N,N-dimethyltryptophan
Serotonin
Tryptamine
Tryptophan
HPLC Separation of Mixture of 12 Amino Acids on Primesep 100 Column
March 11, 2019
| Column | Primesep 100, 4.6×250 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 |
| Class of Compounds |
Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | L-Asparagine (Asn/N), L-Threonine (Thr/T), L-Cysteine (Cys/C), L-Proline (Pro/P), L-Valine (Val/V), DL-Methionine (Met/M), L-Isoleucine (Ile/I), L-Leucine (Leu/L), L-Phenylalanine (Phe/F), L- Tryptophan (Trp/W), L-Histidine (His/H), L-Arginine (Arg/R) |
Application Column
Primesep 100
The Primesep family of mixed-mode columns offers a wide variety of stationary phases, boasting unprecedented selectivity in the separation of a broad array of chemical compounds across multiple applications. Corresponding Primesep guard columns, available with all stationary phases, do not require holders. SIELC provides a method development service available to all customers. Inquire about our specially-tailored custom LC-phases for specific separations.
Select optionsArginine
Asparagine
Cysteine
D-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Cysteine
L-Methionine
L-Threonine
Leucine
Methionine
Phenylalanine
Proline
Tryptophan
Valine
HPLC Separation of Mixture of Essential Amino Acids on Primesep 100 Column
March 11, 2019
| Column | Primesep 100, 4.6×250 mm, 5 µm, 100A |
| Mobile Phase | MeCN/H2O – 25/75% |
| Buffer | Gradient H2SO4 0.05-0.2% 25 min |
| Flow Rate | 1.0 ml/min |
| Detection | UV, 200 nm |
| Class of Compounds |
Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | L-Threonine (Thr/T), L-Valine (Val/V), DL-Methionine (Met/M), L-Isoleucine (Ile/I), L-Leucine (Leu/L), L-Phenylalanine (Phe/F), L-Histidine (His/H), L- Tryptophan (Trp/W) |
Application Column
Primesep 100
The Primesep family of mixed-mode columns offers a wide variety of stationary phases, boasting unprecedented selectivity in the separation of a broad array of chemical compounds across multiple applications. Corresponding Primesep guard columns, available with all stationary phases, do not require holders. SIELC provides a method development service available to all customers. Inquire about our specially-tailored custom LC-phases for specific separations.
Select optionsD-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Histidine hydrochloride monohydrate
L-Isoleucine
L-Methionine
L-Threonine
Methionine
Phenylalanine
Tryptophan
Valine
Generic Screening Method for Complex Mixtures on Primesep 200
October 15, 2015
| 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 |
| 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 Column
Primesep 200
Column Diameter: 4.6 mm
Column Length: 150 mm
Particle Size: 5 µm
Pore Size: 100 A
Column options: dual ended
2,6-Lutidine
Amitriptyline
Benzoic Acid
Benzylamine
DOPA (3,4-dihydroxy-L-phenylalanine)
Epinephrine
Ethylparaben
Homovanillic Acid
Hydroxytryptophan
Methylparaben
Phenol
Toluene
Tryptophan
Uracil
HPLC Separation of Amino Acids on Obelisc R Column
October 4, 2007
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.
| Column | Obelisc R, 4.6×250 mm, 5 µm, 100A |
| Mobile Phase | MeCN/H2O – 5/95% |
| Buffer | AmFm |
| Flow Rate | 1.0 ml/min |
| Detection | UV, 250 nm |
| Class of Compounds |
Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | Amino acids |
Application Column
Obelisc R
SIELC has developed the Obelisc™ columns, which are mixed-mode and utilize Liquid Separation Cell technology (LiSC™). These cost-effective columns are the first of their kind to be commercially available and can replace multiple HPLC columns, including reversed-phase (RP), AQ-type reversed-phase, polar-embedded group RP columns, normal-phase, cation-exchange, anion-exchange, ion-exclusion, and HILIC (Hydrophilic Interaction Liquid Chromatography) columns. By controlling just three orthogonal method parameters - buffer concentration, buffer pH, and organic modifier concentration - users can adjust the column properties with pinpoint precision to separate complex mixtures.
Select optionsAspartame
Phenylalanine
Tryptophan
HPLC Separation of Phenylalanine, Glucosamine, and Tryptophan on Mixed-Mode Column
October 4, 2007
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
| Column | Primesep 100, 2.1×100 mm, 5 µm, 100A |
| Mobile Phase | MeCN/H2O |
| Buffer | AmFm |
| Flow Rate | 0.25 ml/min |
| Detection | ELSD |
| Class of Compounds |
Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | Phenylalanine, Glucosamine, Tryptophan |
Application Column
Primesep 100
The Primesep family of mixed-mode columns offers a wide variety of stationary phases, boasting unprecedented selectivity in the separation of a broad array of chemical compounds across multiple applications. Corresponding Primesep guard columns, available with all stationary phases, do not require holders. SIELC provides a method development service available to all customers. Inquire about our specially-tailored custom LC-phases for specific separations.
Select optionsPhenylalanine
Tryptophan
HPLC Separation of Amino Acids, Bases, Acids, and Neutrals on Obelisc R
March 3, 2007
Separating basic, acidic and zwitterionic compounds in one run in reverse-phase HPLC can be very challenging. The methods might require the use of ion-pairing reagents and complex gradients that can make MS-compatibility difficult. Obelisc R column which has both positive and negative ion-pairs embedded in the stationary phase allows for fine tuning and separation of a wide range of compounds with different ionic properties. Acids, bases, amino acids and neutral compounds were separated isocratically in one run using a simple MS-compatible mobile phase of acetonitrile (ACN) and water with Ammonium Acetate (AmAc) buffer. Can also be UV detected at 250nm.
| Column | Obelisc R, 4.6×250 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 |
| Class of Compounds |
Drug, Acid, Bases, Neutral, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid |
| Analyzing Compounds | Amino acids |
Application Column
Obelisc R
SIELC has developed the Obelisc™ columns, which are mixed-mode and utilize Liquid Separation Cell technology (LiSC™). These cost-effective columns are the first of their kind to be commercially available and can replace multiple HPLC columns, including reversed-phase (RP), AQ-type reversed-phase, polar-embedded group RP columns, normal-phase, cation-exchange, anion-exchange, ion-exclusion, and HILIC (Hydrophilic Interaction Liquid Chromatography) columns. By controlling just three orthogonal method parameters - buffer concentration, buffer pH, and organic modifier concentration - users can adjust the column properties with pinpoint precision to separate complex mixtures.
Select optionsBenzoic Acid
Benzonitrile
Benzylamine
Phenol
Phenylalanine
Pyridine
Toluene
Tryptophan
