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Amino Acids

Amino acids are the building blocks of proteins and play a central role in almost all biological processes. In the human body, they are essential for the formation of tissue, the repair of cells and the production of enzymes and hormones. There are 20 different amino acids, some of which are labelled "essential" because the body cannot produce them itself and they must therefore be obtained from food. Amino acids are also crucial for the metabolism, the immune system and the regulation of numerous physiological functions, such as the transport and storage of nutrients.

 

Amino acid analysis is therefore of great importance as it provides precise information on the quantity and profile of amino acids in biological samples, food or pharmaceutical products. These analyses are essential for assessing nutritional status, diagnosing metabolic disorders and ensuring the quality of food and food supplements. In medicine, amino acid analysis helps to detect imbalances that may indicate health problems, such as liver disease or genetic metabolic disorders. In the food industry, it contributes to the control and optimisation of protein content, which is particularly important for quality assurance and compliance with legal requirements.

Overview of amino acids and classification into different groups

Overview of the different amino acids and the polarity of the side chains.

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AccQ-Tag Cell Culture Chemistry Kit - Automation;
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Technical Data

Derivatisation of amino acids

In order to detect amino acids using fluorescence or to separate them using the reversed phase, amino acids must be derivatised. The classic method uses separation of the amino acids by ion exchange chromatography with subsequent post-column derivatisation to enable detection with a fluorescence detector. Ortho-phthaldialdehyde (OPA), 9-fluorenyl-methoxycarbonyl-chloride (FMOC-Cl), ninhydrin or fluorescamine can be used as reagents.

 

The most modern technique for the derivatisation of amino acids is pre-column derivatisation with ortho-phthaldialdehyde (OPA) and subsequent separation using reversed phase chromatography and subsequent fluorescence detection. The advantages here are the fast analysis times and the high sensitivities. However, a major disadvantage is that OPA only reacts with primary amines. This derivatisation method does not work for secondary amines such as proline.

 

The reagent 9-fluorenyl-methoxycarbonyl-chloride (FMOC-Cl) is therefore used for the pre-column derivatisation of secondary amines. After this derivatisation, the amino acids can also be separated using reversed-phase chromatography and detected using fluorescence.

On-line and off-line derivatisation

Additional hardware is required for post-column derivatisation. The derivatisation reagent must be added to the amino acids in precise doses after the separation of the amino acids. This is achieved using an additional pump after the separation. After the reagent has been added, the amino acids need a certain amount of time to react. Therefore, a loop or a specially woven capillary is used to obtain a specific reaction time. An example setup can be found in the figure on the right.

 

An on-line solution can also be implemented for pre-column derivatisation. For this, only the arrangement of the post-column derivatisation has to be changed so that the derivatisation takes place before the column. However, this derivatisation can be carried out off-line, which means that there is no additional hardware requirement for the HPLC system. The sample is already derivatised before it is injected into the HPLC system.

Schematic representation of post-column derivatization in amino acid analysis

Post-column derivatisation - Structure of the HPLC system

Analysis of amino acids without derivatisation

It is also possible to separate and detect the amino acids without derivatisation. As in post-column derivatisation, the separation takes place using ion exchange or other special columns. The subsequent detection is then carried out using mass spectrometry (MS). The Intrada Amino Acid from Imtakt should be highlighted here as a special column for the separation of non-derivatised amino acids. With these columns it is possible to analyse the 20 amino acids within 10 minutes with MS/MS detection without derivatisation.

Chiral separation of amino acids

The chiral separation of all amino acids has so far been accomplished in different chromatographic separation runs, resulting in different methods to analyse all enantiomers. The new Vaast column from Daicel Chiral Technology enables the chiral separation of all natural amino acids in less than 5 minutes in one run. In addition, impurities in Fmoc-protected amino acids can also be investigated in more detail using an alternative derivatisation. Kits are also available for this derivatisation.

Applications

Chiral separation of 21 natural amino acids with Chiral Vaast

The amino acids are derivatised using AQC (6-aminoquinolyl-N-hydroxysuccinimidyl carbamate).

Peak identities

AQC-Ile = AQC-Isoleucine AQC-Val = AQC-Valine AQC-Leu = AQC-Leucine AQC-Pro = AQC-Proline AQC-Phe = AQC-PhenylalanineAQC-Met = AQC-Methionine AQC-Ala = AQC-Alanine AQC-Thr = AQC-Threonine AQC-Hse = AQC-Homoserine AQC-Trp = AQC-TryptophanAQC-Tyr = AQC-Tyrosine AQC-Cys = AQC-Cysteine AQC-Ser = AQC-Serine AQC-Gln = AQC-Glutamine AQC-Gly = AQC-GlycineAQC-Asn = AQC-Asparagine AQC-Lys = AQC-Lysine AQC-His = AQC-Histidine AQC-Glu = AQC-Glutamine AQC-Asp = AQC-Asparagine AQC-Arg = AQC-Arginine

Test conditions

Column: Vaast 100x2.1mm, 1.7µm

Underivatised amino acid analysis with Imtakt Intrada Amino Acid

Determination of 20 amino acids

Separation of different amino acid standards with the Intrada Amino Acid from Imtakt

Peak identities

Trp = tryptophan Phe = phenylalanine Tyr = tyrosine Met = methionine Leu = leucine , Ile= isoleucine Val = valine Glu = glutamic acid Pro = proline Thr = threonineAsp = aspartic acid Ala = alanine Ser = serine Gln = glutamine Lys = lysine Gly = glycine Asn = asparagine Cys = cysteine His = hystidine Arg = arginine

 

Test conditions

Column: Intarda Amino Acid 50 x 3 mm

Pre-column derivatisation of amino acids with OPA and FMOC using GL Sciences Inertsil ODS-4 HP

Separation of amino acids after pre-column derivatization with the Inertsil ODS-4 HP from GL Sciences

Peak identities

1. OPA-Aspartic Acid 2. OPA-Glutamic Acid 3. OPA-Asparagine 4. OPA-Serine 5. OPA-Glutamine 6. OPA-Histidine 7. OPA-Glycine 8. OPA-Threonine 9. OPA-Citruｌline 10. OPA-Arginine 11. OPA-Alanine 12. OPA-GABA(4-aminobutanoic acid) 13. OPA-Tyrosine 14. OPA-Cys-Cys 15. OPA-Valine 16. OPA-Methionine 17. OPA-Tryptophan 18. OPA-Phenylalanine 19. OPA-Isoleucine 20. OPA-Leucine 21. OPA-Lysine 22. Fmoc-Proline

 

Test conditions

Column: Inertsil ODS-4 HP 150x3.0mm 3µm (5020-14005)

 

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Manufacturer overview

Manufacturer AMT

Separation ModeProduct Line
HPLC - HILIC
  • HALO 90Å Glycan, 2.7µm
  • HALO 90Å Penta-HILIC, 2.7µm
HPLC - Reversed Phase
  • HALO 90Å AQ-C18, 2.7µm

 

Logo of the manufacturer Advanced Materials Technology (AMT) with the HALO brand logo

Manufacturer ChromaNik

Separation ModeProduct Line
HPLC - Reversed Phase
  • SunShell RP-AQUA, 2.6µm
  • SunShell C18, 2.6µm
  • SunShell PFP, 2.6µm
  • SunShell PFP&C18, 2.6µm
  • SunShell Biphenyl, 2.6µm
  • SunArmor NH2, 5µm
UHPLC - Reversed Phase
  • Sunniest C18-HT, 2µm
Logo of the manufacturer ChromaNik

Manufacturer Concise

Separation ModeProduct Line
HPLC - IEX
  • AminoSep
  • Amino Acid
Logo of the manufacturer Concise Separations

Manufacturer GL Sciences

Separation ModeProduct Line
HPLC - Reversed Phase
  • Inertsil CN-3, 5µm
  • Inertsil ODS-2, 5µm
  • Inertsil ODS-4, 3µm
  • Inertsil ODS-4 HP, 3µm
  • Inertsil ODS-4V, 5µm
  • InertSustain C18, 3µm
  • InertSustain C30, 5µm
  • InertSustain PFP HP, 3µm
  • InertSustainSwift C18, 5µm
UHPLC - Reversed Phase
  • Inertsil ODS-4, 2µm
HPLC - HILIC
  • Inertsil Diol, 5µm
  • InertSustain Amide, 5µm
GC
  • InertCap 5MS
Logo of the manufacturer GL Sciences

Manufacturer Helix

Separation ModeProduct Line
HPLC - Mixed-Mode
  • Amaze HD, 5µm
  • Amaze SC, 5µm
Logo of the manufacturer Helix Chromatography

Manufacturer Sepax

Separation ModeProduct Line
HPLC - Reversed Phase
  • GP-C18, 5µm
Logo of the manufacturer Sepax

Manufacturer Shodex

Separation ModeProduct Line
HPLC - Reversed Phase
  • RSpak NN-814
HPLC - HILIC
  • HILICpak VC-50 2D
  • Asahipak NH2P-40 2D
HPLC - Ion chromatography
  • IC YS-50
  • CXpak P-421S
Logo of the manufacturer Shodex

Manufacturer Tosoh

Separation ModeProduct Line
HPLC - Reversed Phase
  • TSKgel ODS-100V, 5µm
Logo of the manufacturer Tosoh Bioscience

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