Tryptophan

Tryptophan structural formula

CAS Number54-12-6
Molecular FormulaC11H12N2O2
Molecular Weight204.230
InChI KeyQIVBCDIJIAJPQS-UHFFFAOYSA-N
LogP-1.05
Synonyms
  • dl-Tryptophan
  • Tryptophan
  • 54-12-6
  • (.+-.)-Tryptophan
  • (RS)-Tryptophan
  • 1H-Indole-3-alanine
  • DL-triptofano
  • DL-Tryptophane
  • DL-α-Amino-3-indolepropionic acid
  • NSC 13118
  • TRYPTOPHAN, DL-
  • DL-alpha-Amino-3-indolepropionic acid
  • EINECS 200-194-9
  • Racemic Tryptophan
  • (+-)-Tryptophan
  • DL-Trytophan
  • DL-Trytophane
  • UNII-X9U7434L7A
  • 2-amino-3-(1H-indol-3-yl)propanoic acid
  • Htrp
  • Trp
  • W
  • alpha-amino-beta-3-indolepropionic acid
  • beta-3-indolylalanine
  • triptofano
  • tryptophane

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

HPLC Method for Analysis of Mixture of Tryptophan and its Catabolites on Primesep 100 Column by SIELC Technologies

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.

.

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

ColumnPrimesep 100, 4.6 x 150 mm, 5 µm, 100 A
Mobile PhaseGradient MeCN 5-50% in 10 min, with 2 min hold afterwards
BufferGradient H2SO4 from 0.1-0.2% in 10 min, with 2 min hold afterwards
Flow Rate1.0 ml/min
DetectionUV 220 nm

Description

Class of CompoundsEssential Amino Acid Tryptophan and its Catabolites
Analyzing CompoundsTryptophan, 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

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Application Analytes:
3-Hydroxyanthranilic acid
3-Hydroxykynurenine
Kynurenine
Picolinic Acid
Tryptophan

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

HPLC Separation of Mixture of Nine Essential Amino acids and Arginine on Newcrom AH Column

September 25, 2020


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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.

Condition

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

 

Description

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.

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Application Analytes:
Arginine
Histidine
Isoleucine
L-Threonine
Leucine
Lysine
Methionine
Phenylalanine
Tryptophan
Valine
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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.

Condition

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

 

Description

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.

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Application Analytes:
N,N-Dimethyl-5-methoxytryptamine
N,N-Dimethyltryptamine
N,N-dimethyltryptophan
Serotonin
Tryptamine
Tryptophan
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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

March 11, 2019

 

Condition

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

 

Description

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.

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Application Analytes:
Amino Acids
Arginine
Asparagine
Cysteine
D-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Cysteine
L-Methionine
L-Threonine
Leucine
Methionine
Phenylalanine
Proline
Tryptophan
Valine
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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

March 11, 2019

 

Condition

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

 

Description

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.

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Application Analytes:
Amino Acids
D-Isoleucine
D-Leucine
D-Valine
DL-Isoleucine
Histidine
Isoleucine
L-Histidine hydrochloride monohydrate
L-Isoleucine
L-Methionine
L-Threonine
Methionine
Phenylalanine
Tryptophan
Valine
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

Generic Screening Method for Complex Mixtures on Primesep 200

October 15, 2015

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 Column

Primesep 200

Column Diameter: 4.6 mm
Column Length: 150 mm
Particle Size: 5 µm
Pore Size: 100 A

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

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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.

Condition

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

 

Description

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.

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Application Analytes:
3-Aminobenzoic Acid
Aspartame
Phenylalanine
Tryptophan

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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

Condition

Column Primesep 100, 2.1×100 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmFm
Flow Rate 0.25 ml/min
Detection ELSD

 

Description

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.

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Application Analytes:
Glucosamine
Phenylalanine
Tryptophan

Application Detection:
ELSD Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

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.

Condition

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

 

Description

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 options
Application Analytes:
2,6-Lutidine
Benzoic Acid
Benzonitrile
Benzylamine
Phenol
Phenylalanine
Pyridine
Toluene
Tryptophan

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.