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| Product Name | Fmoc-Ser(tBu)-OH |
|---|---|
| Synonyms | Fmoc-O-tert-butyl-L-serine; Fmoc-Ser(tBu)-OH |
| Catalog No. | AS0706 |
| CAS Number | 71989-33-8 |
| Molecular Formula | C22H25NO5 |
| Molecular Weight | 383.44 g/mol |
| Appearance | White powder |
| Melting Point | 125–140°C |
| Specific Rotation | +25° ± 2.5° (C=1 in EtOAc) |
| Storage Temperature | Cool, dry place (≤25°C) |
| Side-Chain Protection | tert-Butyl-protected hydroxyl |
| Primary Application | Fmoc-SPPS |
Product Overview
Fmoc-Ser(tBu)-OH is the conventional Fmoc-protected serine building block used in peptide synthesis.
The α-amino group is protected with Fmoc, while the serine side-chain hydroxyl is protected as a tert-butyl ether.
The tBu group remains stable during repeated Fmoc deprotection cycles and is removed during final acidic cleavage.
Applications in Peptide Synthesis
| Application | Role of Fmoc-Ser(tBu)-OH |
|---|---|
| Fmoc-SPPS | Standard protected L-serine building block |
| Ser-Containing Peptides | Protects the hydroxyl during elongation |
| Polar Peptides | Introduces a small hydroxyl-containing residue after cleavage |
| Peptide Libraries | Supports routine Ser incorporation |
| SAR Studies | Useful for evaluating hydrogen-bonding and polarity |
| Modified Peptides | Starting point for many Ser-containing peptide designs |
Why Protect Serine with tBu?
An unprotected serine hydroxyl can participate in unwanted acylation during peptide synthesis.
tBu protection minimizes O-acylation while remaining compatible with the standard Fmoc/tBu strategy.
During final TFA cleavage, tBu is removed and the native serine hydroxyl is regenerated.
For protecting-group selection, see Choosing Fmoc-Protected Amino Acids for Peptide Synthesis.
Serine as a Modification Site
Serine is biologically important because its hydroxyl can participate in:
phosphorylation
glycosylation
hydrogen bonding
enzyme recognition
polarity control
However, Fmoc-Ser(tBu)-OH is intended to produce ordinary Ser after final deprotection.
If the target peptide requires phosphoserine, glycosylated serine or another site-specific Ser modification, a specialized building block or orthogonal strategy may be required.
Alan Scientific practical view: the correct serine building block depends on the final chemical state required at the hydroxyl—not simply on the amino-acid sequence.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
📎 MSDS_Fmoc-Ser(tBu)-OH_AS0706.pdf
Related Technical Resources
Explore Standard Fmoc-Amino Acids.
Read Amino Acids & Peptide Building Blocks.
For phosphorylated or otherwise modified peptides, see Custom Peptide Synthesis.
Why Source Peptide Building Blocks from Alan Scientific?
Alan Scientific supplies standard and specialized protected amino acids for routine SPPS and advanced peptide modification projects.
Research Use Only