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Fmoc-Lys(Aloc)-OH is a doubly protected L-lysine derivative for solid-phase peptide synthesis (SPPS). It carries two orthogonal protecting groups: Fmoc on the α-amino group (removed by piperidine) and Alloc on the ε-amino side chain (removed by Pd(0) catalysis). This orthogonality allows selective side-chain modification—such as attaching dyes, biotin, drugs, or lipids—while the peptide chain is still on resin. It enables branched and cyclic peptide architectures. Compatible with standard Fmoc-SPPS protocols, it is available at ≥98% purity. Key selling points: true three-way orthogonality, mild deprotection, broad compatibility, and versatile applications across drug discovery, diagnostics, and biomaterials.
Specifications of Fmoc-Lys(aloc)-OH CAS 146982-27-6 COA:
Items | Specifications | Results |
Appearance | White powder | White powder |
Solubility | 0.5mmole in 1ml DMF clearly soluble | Clearly soluble |
IR Spectrum | In accordance with structure | In accordance with structure |
Specific Rotation[α]D20 | -12.0±1.5°(C=1,DMF) | -11.5°（C=1，DMF） |
Optical Purity(HPLC) | ≤0.30% D-enantiomer | Not detected |
Water(K.F) | ≤1.0% | 0.4% |
Fmoc-β-Ala-OH(HPLC) | ≤0.10% | 0.006% |
Fmoc-Lys-OH.HCL(HPLC) | ≤0.10% | Not detected |
Fmoc-Lys(Alloc)-Lys(Alloc)-OH(HPLC) | ≤0.10% | ＜0.10% |
Fmoc-β-Ala-Lys(Alloc)-OH(HPLC) | ≤0.10% | ＜0.10% |
Free Lys TLC Analysis | ＜0.05% | |
Any other impurity | ≤0.20% | 0.08% |
Purity(HPLC) | ≥99.0%（Area%） | 99.78% |
Assay(AT) | ≥95.0%（AT） | 98.2% |
Acetic acid ions(IC) | ≤100mg/kg | 34.53mg/kg |
Residual solvent(GC) | ≤0.50% Ethyl acetate ≤0.50% petroleum ether ≤0.072%Tetrahydrofuran | 0.003% 0.24% 0.007% |
Conclusion | The product conforms to the above specifications. | |
Product Name:Fmoc-Lys(aloc)-OH
CAS:146982-27-6
MF:C25H28N2O6
Melting point :87-91°C
form:powder
color:White
Uses:
Fmoc-Lys(Aloc)-OH — Comprehensive Overview
Fmoc-Lys(Aloc)-OH (CAS: 146982-27-6) is a specially protected derivative of the natural amino acid L-lysine, designed for use in solid-phase peptide synthesis (SPPS). Its full chemical name is:
Nα-(9-Fluorenylmethyloxycarbonyl)-Nε-(Allyloxycarbonyl)-L-lysine
It features two orthogonal protecting groups on the two amino groups of lysine:
| Position | Protecting Group | Removal Condition |
|---|---|---|
| α-amino (backbone) | Fmoc (9-fluorenylmethyloxycarbonyl) | Mild base (e.g., piperidine/DMF) |
| ε-amino (side chain) | Alloc (allyloxycarbonyl) | Pd(0)-catalyzed reaction (e.g., Pd(PPh₃)₄ with a nucleophile like morpholine or phenylsilane) |
Molecular Formula: C₂₅H₂₈N₂O₆
Molecular Weight: 452.50 g/mol
Appearance: White to off-white powder
Melting Point: 87–91 °C
Optical Rotation: [α]²⁰/D −12±1° (c = 1% in DMF)
Solubility: Soluble in DMF, DCM, chloroform, ethyl acetate, DMSO, acetone
Storage: 2–8 °C, under inert gas, air- and heat-sensitive
Core Concept: Orthogonal Protection
The defining feature of Fmoc-Lys(Aloc)-OH is its orthogonal protection strategy. The two protecting groups can be removed independently under completely different, non-interfering conditions:
Fmoc is stable to acid and Pd-catalyzed conditions, but is cleaved by mild base (piperidine).
Alloc is stable to both acid and base, but is selectively removed by palladium(0)-catalyzed allyl transfer.
This means a chemist can expose the ε-amino group of lysine while the peptide chain is still being assembled on the resin, without disturbing any other protecting groups (Fmoc, Boc, t-Bu, etc.) in the molecule. This level of precision is what makes this reagent indispensable.
Key Uses & Applications
1. Solid-Phase Peptide Synthesis (SPPS)
Fmoc-Lys(Aloc)-OH is a standard building block in Fmoc-SPPS. It is coupled into a growing peptide chain via its α-amino position (after Fmoc removal), while the Alloc group keeps the ε-amino side chain protected and inert during chain elongation.
2. Side-Chain Functionalization of Lysine
After the peptide chain is assembled, the Alloc group can be selectively removed on-resin using Pd(PPh₃)₄, exposing the ε-amino group. This free amine can then be conjugated to:
Fluorescent dyes (e.g., FAM, rhodamine) for imaging
Biotin for affinity purification or detection
PEG chains for improved pharmacokinetics
Lipids for membrane anchoring
Drugs or cytotoxic payloads for antibody-drug conjugate (ADC) mimics
Radioisotopes for diagnostic or therapeutic applications
3. Synthesis of Branched Peptides
The exposed ε-amino group serves as a branching point for building multi-antigen peptides (MAPs) or other branched architectures. Additional amino acid chains can be elongated from the lysine side chain.
4. Synthesis of Cyclic Peptides
By selectively deprotecting the Alloc group on-resin, the ε-amino group can be cyclized with a free carboxyl group elsewhere in the peptide (head-to-side-chain cyclization) or with another side chain, forming macrocylic or cyclic peptide structures. Cyclic peptides often show enhanced metabolic stability and receptor selectivity.
5. Peptide-Based Biomaterials
Researchers use Fmoc-Lys(Aloc)-OH to synthesize self-assembling peptides for hydrogels and tissue-engineering scaffolds. Side-chain functionalization allows tuning of material properties such as cell adhesion, mechanical strength, and drug-release kinetics.
6. Pharmaceutical & Drug Development
Targeted drug precursors: For example, Fmoc-D-Lys(Aloc)-OH has been used in the solid-phase synthesis of prostate cancer-targeting drug precursors incorporating DOTA chelators.
Cationic antimicrobial peptides: Lipid-modified cationic peptides synthesized using this building block have been studied against multi-drug resistant breast cancer cells.
Dental/orthopedic implant coatings: Peptides designed to prevent bacterial infection on metallic implants.
Selling Points (Why Choose Fmoc-Lys(Aloc)-OH?)
If you are evaluating this compound for procurement or considering it for a product catalog, here are the key value propositions:
✅ True Orthogonality
The Fmoc/Alloc pair provides three-way orthogonality (base, acid, Pd⁰) when combined with standard acid-labile side-chain protecting groups (t-Bu, Boc, Trt). This is the gold standard for complex peptide synthesis where multiple deprotection events must occur in a defined sequence without cross-reactivity.
✅ On-Resin Side-Chain Modification
Unlike lysine derivatives protected with acid-labile groups (e.g., Boc), the Alloc group survives the repetitive TFA-free Fmoc deprotection cycles (piperidine/DMF). This means the ε-amino group remains protected throughout chain assembly and can be selectively unveiled while the peptide is still attached to the resin — enabling on-resin labeling, branching, or cyclization before final cleavage.
✅ Mild & Selective Deprotection
Alloc removal uses Pd(0) catalysis under near-neutral conditions, which does not affect:
Fmoc groups
t-Bu/Boc acid-labile groups
Disulfide bonds
Glycosidic linkages
Most other common protecting groups
This makes it compatible with highly sensitive post-translational modifications (phosphorylation, glycosylation, etc.).
✅ High Purity & Enantiomeric Excess
Commercially available at ≥98% HPLC purity with ≥99.5% enantiomeric excess (ee), ensuring minimal racemization and high-fidelity peptide assembly.
✅ Broad Compatibility
Fully compatible with:
Standard Fmoc-SPPS protocols and coupling reagents (HBTU, HATU, DIC/Oxyma, etc.)
Common resin systems (Wang, Rink amide, 2-CTC, etc.)
Automated peptide synthesizers
Both small-scale research and multi-gram production
✅ Versatility Across Research Areas
A single building block that serves diverse fields:
Drug discovery (peptide therapeutics, ADCs, targeted delivery)
Diagnostics (fluorescent/biotin-labeled peptides)
Biomaterials (hydrogels, scaffolds)
Chemical biology (activity-based probes, peptide arrays)
✅ Established Supply Chain
Available from major suppliers including Sigma-Aldrich/Merck, TCI, MCE, Novabiochem, and specialized Chinese manufacturers, in scales from 1 g to multi-kilogram quantities, with competitive pricing (e.g., ~$104/5 g from TCI as of late 2025).
Summary
Fmoc-Lys(Aloc)-OH is a cornerstone reagent in modern peptide chemistry. Its unique Fmoc + Alloc orthogonal protection on the α- and ε-amino positions of lysine enables precise, sequential control over peptide synthesis — allowing chemists to build complex architectures (branched, cyclic, side-chain-modified peptides) that would be impossible with standard lysine derivatives. Its mild deprotection conditions, high compatibility, and proven track record across pharmaceutical, diagnostic, and biomaterial applications make it an essential tool in any peptide synthesis laboratory.
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Wuhan Fortuna Chemical Co.,Ltd is a professional manufacturer which provide Fmoc-Lys(aloc)-OH with good quality and best price, welcome to contact us to get COA/TDS/MSDS of Fmoc-Lys(aloc)-OH.
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