Fmoc-AEEEA, or Fmoc-8-amino-3,6-dioxaoctanoic acid, is a building block used in solid-phase peptide synthesis (SPPS) to introduce a hydrophilic, flexible spacer into peptides. It’s a PEG-like derivative that improves the water solubility and flexibility of the resulting peptides without using traditional PEG polymers. The Fmoc group provides base-labile N-terminal protection for SPPS. Incorporating Fmoc-AEEEA enhances peptide solubility, reduces aggregation, and can improve pharmacokinetics, making it valuable for drug delivery, diagnostics, and biomaterials.
Appearance
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White to off-white solid powder.
Source
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Synthetically produced via chemical synthesis.
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Commercially available from peptide reagent suppliers and specialized chemical vendors.
Molecular Weight and Structure
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Approximately 355.4 g/mol (C19H19NO6), variable with hydrate/salt forms.
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Consists of a Fmoc protecting group at the N-terminus and an AEEEA spacer (two ethylene glycol units plus a carboxyl terminus).
Biological Activity
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Inactive as a standalone molecule.
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Incorporated AEEEA improves physical properties like solubility and flexibility in larger peptides.
Purity and Microbial Contamination
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Purity: Typically ≥ 95% by HPLC.
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Low or minimal microbial contamination; suppliers provide COAs.
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Tested with LAL assay and sterility assessments.
Identity and Quality Control
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MS confirms molecular weight.
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NMR (¹H and ¹³C) verifies structure.
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IR spectroscopy confirms functional groups.
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HPLC determines purity.
Shelf Life and Storage
| Feature | Description |
|---|---|
| Shelf Life | Typically 1–2 years if stored properly; consult supplier COA |
| Storage | Store at –20°C or below under inert atmosphere in sealed container; protect from moisture/light; avoid freeze-thaw cycles |
Application
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SPPS building block for hydrophilic spacers.
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Synthesis of PEGylated peptides and peptidomimetics.
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Drug delivery and diagnostic peptide design.
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Construction of biomaterials with specific peptide properties.
Key Characteristics
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Fmoc-protected for base-labile N-terminal deprotection.
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PEG-like AEEEA spacer promotes flexibility and solubility.
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Reduces peptide aggregation.
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Versatile coupling in peptide sequences.
Citation
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Overview of PEG-like amino acid spacers in peptide synthesis:
https://pubmed.ncbi.nlm.nih.gov/28238639/ -
Incorporation of PEG-like spacers such as AEEEA for improving peptide solubility:
https://pubs.acs.org/doi/10.1021/acs.jmedchem.1c00565 -
Solid-phase peptide synthesis methods using Fmoc chemistry:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6526649/ -
Effects of α-aminoisobutyric acid (Aib) and related residues on peptide conformation:
https://www.sciencedirect.com/science/article/pii/S0022283618300638 -
Studies on PEGylated peptide drug delivery systems:
https://doi.org/10.1002/anie.202001378 -
Peptidomimetic synthesis including PEG-like spacer strategies:
https://pubmed.ncbi.nlm.nih.gov/32890023/ -
Fmoc-protected amino acid derivatives for peptide assembly:
https://doi.org/10.1016/j.tet.2014.11.058 -
PEG-based linkers and spacers in peptide therapeutics:
https://pubmed.ncbi.nlm.nih.gov/19382616/ -
Applications of hydrophilic spacers for reducing peptide aggregation:
https://pubmed.ncbi.nlm.nih.gov/32285715/ -
Chemical databases for Fmoc-AEEEA structure and properties:
https://pubchem.ncbi.nlm.nih.gov/compound/5372142
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