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| Product Name | Fmoc-Orn(Boc)-OH |
|---|---|
| Synonyms | Nδ-Boc-Nα-Fmoc-L-ornithine; Fmoc-L-Orn(Boc)-OH |
| Catalog No. | AS2057 |
| CAS Number | 109425-55-0 |
| Molecular Formula | C25H30N2O6 |
| Molecular Weight | 454.52 g/mol |
| SMILES | CC(C)(C)OC(=O)NCCCC@HC(O)=O |
| Storage Temperature | 2–8°C |
| Appearance | White to off-white solid |
| Melting Point | 111–115°C (reference) |
| Functional Groups | Fmoc-protected α-amino group; Boc-protected δ-amino group; carboxylic acid |
| Primary Application | Fmoc solid-phase peptide synthesis (SPPS) |
Product Overview
Fmoc-Orn(Boc)-OH, also known as Nδ-Boc-Nα-Fmoc-L-ornithine, is a protected L-ornithine derivative used as an amino acid building block in Fmoc-based solid-phase peptide synthesis (SPPS).
The α-amino group is protected by Fmoc, while the ornithine side-chain δ-amino group is protected by Boc. This orthogonal protecting-group strategy helps prevent unwanted side-chain reactions during peptide chain assembly while allowing the ornithine residue to be incorporated using standard Fmoc-SPPS chemistry.
Ornithine is a non-proteinogenic amino acid structurally related to lysine, with one fewer methylene group in its side chain. Its additional amino functionality makes ornithine useful in the design of modified peptides, cyclic peptides, peptide conjugates, and structure–activity relationship studies.
Applications in Peptide Synthesis
| Application | Role of Fmoc-Orn(Boc)-OH |
|---|---|
| Fmoc Solid-Phase Peptide Synthesis | Incorporation of protected L-ornithine residues into synthetic peptide sequences |
| Modified Peptide Synthesis | Provides a side-chain amino functionality that can be used for downstream peptide modification |
| Cyclic Peptide Synthesis | Supports peptide designs in which the ornithine side chain participates in cyclization strategies |
| Peptide Conjugation | The ornithine side-chain amino group can provide a functional handle for selected conjugation approaches after deprotection |
| Peptide Library Synthesis | Building block for sequence-diverse peptide libraries containing non-proteinogenic amino acids |
| Structure–Activity Relationship Studies | Preparation of ornithine-containing peptide analogs to evaluate the effects of side-chain length and functionality |
| Medicinal Chemistry Research | Used in the development and optimization of biologically active peptide analogs |
Fmoc-Orn(Boc)-OH in Fmoc-SPPS
During Fmoc-SPPS, Fmoc-Orn(Boc)-OH can be activated and coupled to a resin-bound peptide chain while the α-amino group remains protected by Fmoc. Following coupling, standard Fmoc deprotection exposes the α-amino group for the next peptide elongation cycle.
The Boc group protects the δ-amino side chain of ornithine during repeated coupling and Fmoc-deprotection steps. This helps minimize undesired side-chain reactions during peptide assembly.
During final acidic cleavage and deprotection, the Boc protecting group can be removed according to the selected peptide synthesis and cleavage conditions, exposing the ornithine side-chain amino group in the final peptide.
Role of Ornithine in Modified and Cyclic Peptides
Ornithine contains a side-chain amino group similar to lysine but with a shorter carbon chain. This structural difference can be useful when researchers want to investigate how side-chain length, charge distribution, conformational flexibility, or functional-group positioning affects peptide activity.
The δ-amino group of ornithine can also provide a useful functional handle for selected peptide engineering strategies, including side-chain modification, conjugation, and cyclization.
For this reason, Fmoc-Orn(Boc)-OH is commonly considered when designing peptides that require a protected diamino-acid residue or an alternative to lysine in structure–activity relationship studies.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage, and safety assessment.
📎 MSDS_Fmoc-Orn(Boc)-OH_AS2057.pdf
Related Technical Resources
Learn more about protected amino acids and peptide chain assembly in Solid-Phase Peptide Synthesis (SPPS): A Practical Guide.
Explore additional Standard Fmoc-Amino Acids for peptide synthesis applications.
For complete peptide projects, Alan Scientific also provides Custom Peptide Synthesis including synthesis, purification, modification, and analytical quality control.
Why Source Peptide Building Blocks from Alan Scientific?
We supply protected amino acids and peptide building blocks for research and peptide synthesis applications, with competitive pricing, flexible ordering options, and peptide synthesis technical support.
Researchers can source individual Fmoc amino acids or combine building-block procurement with custom peptide synthesis services according to project needs.