| Product name | Fmoc-Asp(OMpe)-OH |
| Synonym | |
| CAS NO. | 180675-08-5 |
| Appearance | White powder |
| Purity | 98% Min |
| MF | C25H29NO6 |
| MW | 439.5 |
| Related categories | Acid derivatives |
| Transport Information | Non-dangerous goods |
| HS Code | 2924199090 |
| Structural formula |  |
| Product Manager Email | sophia@coreychem.com |
Fmoc-Asp(OMpe)-OH is an important L-aspartic acid protecting monomer specifically designed for solid-phase peptide synthesis (SPPS), particularly the Fmoc strategy.
1.Core Components:
Based on the natural amino acid L-aspartic acid (Asp).
Fmoc protecting group (9-fluorenylmethyloxycarbonyl): protects the α-amino group.
OMpe protecting group (p-toluoylmethyl): protects the side chain β-carboxyl group.
The free α-carboxyl group (-OH): forms a peptide bond with the amino group of the subsequent amino acid.
2.Core Features and Functions:
Protective Effect: The Fmoc group is stable under acidic conditions and can be efficiently removed under mild alkaline conditions (such as piperidine/DMF) to expose the α-amino group for peptide chain extension. The OMpe group is stable under these alkaline conditions, protecting the Asp side chain carboxyl group from side reactions during peptide chain assembly.
Photosensitive Deprotection: The most significant feature of the OMpe protecting group is its photosensitivity. After peptide synthesis, long-wavelength ultraviolet (UV) light can be used to selectively and gently remove the side chain OMpe protecting group.
Orthogonal Protection Strategy: The side chain protecting group (photosensitive OMpe) exhibits good orthogonality with N-terminal protecting groups (base-sensitive Fmoc) and commonly used acid-sensitive side chain protecting groups (such as tBu and Trt), allowing precise control of the deprotection order of different functional groups in multi-step syntheses.
Selective Modification: Selective photodeprotection of the side chain β-carboxyl group is crucial for specific manipulations of Asp residues after synthesis, such as:
Synthesis of peptides or peptide conjugates containing Asp branch points.
Forming side-chain-linked cyclic peptides (e.g., cyclization of the β-carboxyl group of Asp with the amino group of another amino acid residue).
Specifically attaching other functional molecules (such as labels and drug carriers) to the aspartic acid side chain.
3.Main Application: Used for the introduction of L-aspartic acid residues whose side chain β-carboxyl groups are protected by a photosensitive OMpe group in Fmoc-SPPS. This reagent is particularly suitable for the synthesis of complex peptides or peptide-derived compounds requiring precise and selective activation or modification of the aspartic acid side chain carboxyl group in late-stage synthesis.
4.Important Benefit: It provides a powerful tool for site-specific control of aspartic acid side chain reactivity in peptide synthesis and is a key intermediate for the construction of structures containing specific Asp modifications, such as cyclized peptides, branched peptides, and functionalized peptides.
Summary: Fmoc-Asp(OMpe)-OH (CAS 180675-08-5) is an aspartic acid monomer designed specifically for Fmoc peptide synthesis. Its unique photosensitive OMpe side chain protecting group allows precise deprotection and subsequent modification of the aspartic acid β-carboxyl group at specific timings via photoirradiation, making it an indispensable and valuable reagent for the synthesis of peptide structures and functionalization.
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Contact information:
Contact: Sophia Li
Email: sophia@coreychem.com
