Tryptophan

Tryptophan structural formula

CAS Number 54-12-6
Molecular Formula C11H12N2O2
Molecular Weight 204.230 g/mol
InChI Key QIVBCDIJIAJPQS-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 Separation of Amino Acids, Bases, Acids, and Neutrals on Obelisc R
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, 4.6x250 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

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

Condition

Column Primesep 100, 2.1x100 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 Analytes:

Glucosamine
Phenylalanine
Tryptophan

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

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 - 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 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 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 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

HPLC Separation of Biogenic Amines on Primesep 100 Column
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, 4.6x150 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 Analytes:

N,N-Dimethyl-5-methoxytryptamine
N,N-Dimethyltryptamine
N,N-dimethyltryptophan
Serotonin
Tryptamine
Tryptophan

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