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| Product Name | Fmoc-Trp(Boc)-OH |
|---|---|
| Synonyms | Nα-Fmoc-Nin-Boc-L-tryptophan |
| Catalog No. | AS0708 |
| CAS Number | 143824-78-6 |
| Molecular Formula | C31H30N2O6 |
| Molecular Weight | 526.58 g/mol |
| Appearance | White powder |
| Specific Rotation | -20° ± 4° (C=1 in DMF) |
| Storage Temperature | ≤ -15°C |
| Side-Chain Protection | Boc-protected indole nitrogen |
| Primary Application | Fmoc-SPPS |
Product Overview
Fmoc-Trp(Boc)-OH is a protected L-tryptophan building block designed for Fmoc-SPPS.
The α-amino group is Fmoc-protected, while the indole nitrogen is protected by Boc.
Tryptophan is one of the most chemically sensitive standard amino acids because its electron-rich indole ring can participate in acid-mediated and oxidative side reactions.
Applications in Peptide Synthesis
| Application | Role of Fmoc-Trp(Boc)-OH |
|---|---|
| Fmoc-SPPS | Protected L-tryptophan building block |
| Trp-Containing Peptides | Protects the indole nitrogen during synthesis |
| Aromatic Binding Motifs | Introduces a large aromatic heterocycle |
| Fluorescence Studies | Trp provides intrinsic aromatic fluorescence |
| Membrane-Active Peptides | Frequently occurs at membrane interfaces |
| SAR Studies | Useful for aromatic and hydrogen-bonding interactions |
Why Protect Tryptophan with Boc?
The indole ring is chemically more sensitive than many ordinary hydrophobic side chains.
Boc protection can reduce unwanted reactions involving the indole nitrogen during synthesis and final cleavage.
After peptide assembly, the protecting group is removed under acidic cleavage conditions.
Trp Oxidation Is a Major Quality Consideration
Tryptophan can undergo oxidative modification during synthesis, purification or storage.
Potential sources include:
peroxide-containing solvents or reagents
prolonged oxygen exposure
strong oxidizing conditions
inappropriate cleavage/workup chemistry
long-term storage
Oxidized Trp products may generate additional HPLC peaks and altered masses.
Alan Scientific practical view: for Trp-containing peptides, minimizing oxidative damage throughout the complete process is preferable to trying to solve the problem only during final purification.
Cleavage Chemistry Matters
Because tryptophan is sensitive to reactive species generated during strong-acid cleavage, appropriate scavenger systems and cleavage conditions can be important, particularly in sequences containing multiple sensitive residues.
The best cleavage cocktail should therefore be selected according to the entire amino-acid composition of the peptide, not simply the presence of Trp alone.
Tryptophan in Peptide Design
The indole side chain combines:
high aromatic surface area
hydrophobicity
hydrogen-bonding capability
intrinsic fluorescence
This makes Trp particularly important in membrane-active peptides and protein-binding interfaces.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
📎 MSDS_Fmoc-Trp(Boc)-OH_AS0708.pdf
Related Technical Resources
Explore Standard Fmoc-Amino Acids.
Read Amino Acids & Peptide Building Blocks.
For difficult Trp-containing sequences, see Custom Peptide Synthesis.
Why Source Peptide Building Blocks from Alan Scientific?
Alan Scientific supplies standard and specialty peptide building blocks with technical support for synthesis, purification and analytical quality control.
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