Fmoc-Val-Aib-OH is a dipeptide building block used widely in solid-phase peptide synthesis (SPPS), specifically for peptides requiring enhanced structural properties. It pairs valine (Val), a standard hydrophobic amino acid, with α-aminoisobutyric acid (Aib), a non-proteinogenic amino acid renowned for promoting and stabilizing α-helical and 3_10-helical structures. The N-terminal amino group is protected by the base-labile Fmoc (9-fluorenylmethoxycarbonyl) group, enabling controlled synthesis steps. Aib’s conformational constraint supports peptide helicity, facilitating the design of peptides with precise secondary structures, valuable in drug design, biomaterials, and protein folding studies.
Appearance
- White to off-white solid powder
Source
- Chemically synthesized
- Commercially available from peptide synthesis reagent suppliers
Molecular Weight and Structure
- Approximate Molecular Weight: 424.5 g/mol (C₂₃H₂₆N₂O₅)
- Structure includes:
- Fmoc protecting group at N-terminus
- Valine residue
- α-Aminoisobutyric acid (Aib) residue
- Free carboxyl group at C-terminus
Biological Activity
- Inert as a standalone dipeptide
- Biological effects depend on incorporation into larger peptides
- Aib promotes α-helical conformation influencing peptide interactions
- Valine contributes hydrophobic character affecting peptide-membrane or protein interactions
Purity and Microbial Contamination
| Test | Specification |
|---|---|
| Purity (HPLC) | Typically ≥ 95% |
| Microbial contamination | Minimal, with appropriate certificate of analysis (COA) |
Identity and Quality Control
| Test | Specification |
|---|---|
| Mass Spectrometry | Confirms accurate molecular weight |
| NMR Spectroscopy (¹H, ¹³C) | Validates chemical structure |
| Infrared Spectroscopy | Confirms key functional groups |
| HPLC | Determines purity and detects impurities |
| Optical Rotation | Confirms correct stereochemistry of L-Valine |
| Amino Acid Analysis | Validates amino acid composition |
Shelf Life and Storage
| Feature | Description |
|---|---|
| Shelf Life | Typically 1-2 years when stored properly |
| Storage | Store at -20°C or below, in inert atmosphere (argon or nitrogen), sealed container, protected from moisture and light; avoid freeze-thaw cycles |
Application
- SPPS building block for α-helical peptide synthesis
- Peptidomimetic design and synthesis
- Drug discovery, including peptides targeting protein-protein interactions
- Biomaterial design employing α-helical peptides
Key Characteristics
- Fmoc group enables base-labile N-terminal protection/deprotection
- Aib residue introduces helix-promoting conformational constraint
- Valine contributes hydrophobic interactions within peptides
- Soluble in common peptide synthesis solvents such as DMF, DMSO, and acetonitrile
- Versatile for coupling with a broad range of amino acids
Citation
- Search for “Fmoc-Val-Aib-OH peptide synthesis” on PubMed or Google Scholar
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Targeted papers on Aib’s effect on peptide helicity and structure
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Articles on helical and 3_10-helical peptides in drug discovery
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Supplier technical data sheets often contain use cases and references
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