Fmoc-Asn-OH (CAS 71989-16-7), also known as Nα-Fmoc-L-asparagine, is a fundamental Nα-Fmoc-protected amino acid building block for the introduction of asparagine residues in Fmoc-based solid-phase peptide synthesis (SPPS). The molecule consists of the L-asparagine amino acid with its Nα position protected by the base-labile 9-fluorenylmethyloxycarbonyl (Fmoc) group, while the side chain carboxamide remains unprotected.
Fmoc-Asn-OH is the standard building block for the introduction of asparagine residues in Fmoc solid-phase peptide synthesis. As an N-Fmoc-protected form of L-asparagine, Fmoc-Asn-OH enables the efficient incorporation of asparagine into synthetic peptides through standard SPPS protocols. Fmoc-Asn-OH is widely used in the synthesis of peptides and proteins, serving as a fundamental building block that allows for the sequential addition of amino acids to form complex peptide structures. However, users should note that Fmoc-Asn-OH is not compatible with uronium and phosphonium coupling reagents, and alternative coupling strategies should be employed when using this derivative. As one of the most commonly used Fmoc-protected amino acids, Fmoc-Asn-OH is an indispensable component of the synthetic peptide chemist's toolkit, supporting applications ranging from academic research to commercial peptide pharmaceutical manufacturing.
Product Parameters
Parameter
Specification
Product Name
Fmoc-Asn-OH
CAS Number
71989-16-7
Molecular Formula
C₁₉H₁₈N₂O₅
Molecular Weight
354.36 g/mol
Appearance
White to almost white crystalline powder
Melting Point
190°C (dec.)(lit.)
Boiling Point
487.59°C at 760 mmHg
Density
1.3354 g/cm³
pKa
3.68±0.10
Solubility
Soluble in water or 1% acetic acid;
Soluble in DMF
Storage Condition
Sealed in dry , 2–8°C
Product Advantages
1. Standard Building Block for Asparagine Incorporation
Fmoc-Asn-OH is the definitive building block for introducing asparagine residues in Fmoc solid-phase peptide synthesis. Its status as a standard reagent reflects its proven reliability and widespread adoption in the peptide synthesis community.
2. Unprotected Side Chain Simplifies Synthesis
Unlike many other amino acid derivatives that require side-chain protection, Fmoc-Asn-OH features an unprotected carboxamide side chain. This eliminates the need for additional protection/deprotection steps, simplifying synthesis workflows and reducing the risk of side reactions.
3. High Purity for Reliable Peptide Assembly
Cosperpharm supplies Fmoc-Asn-OH with HPLC purity ranging from ≥97.0% to ≥99.0%. High purity ensures efficient coupling, minimizes deletion sequences, and delivers high-quality peptide products.
4. Proven Compatibility with Fmoc SPPS
Fmoc-Asn-OH is fully compatible with standard Fmoc SPPS protocols. However, users should note that it is not compatible with uronium and phosphonium coupling reagents, and alternative coupling strategies should be employed.
5. Broad Application Across Peptide Research
Fmoc-Asn-OH is widely used in the synthesis of peptides and proteins, serving as a fundamental building block for complex peptide structures in both academic and industrial settings.
6. Rigorous Quality Control
Every batch of Fmoc-Asn-OH undergoes comprehensive analytical testing, including HPLC purity, TLC purity, melting point verification, optical rotation, and appearance inspection.
Synthetic Route
Fmoc-Asn-OH is synthesized through the Fmoc protection of L-asparagine:
Step 1 — Fmoc protection: L-Asparagine is reacted with 9-fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) or Fmoc-OSu under basic conditions (typically aqueous sodium carbonate or sodium bicarbonate) to introduce the Fmoc group at the Nα position.
Step 2 — Isolation: The Fmoc-protected product is isolated by extraction and precipitation.
Step 3 — Recrystallization: The crude product is recrystallized to achieve high purity (≥97% to ≥99% HPLC).
Note: Detailed synthetic protocols are well-established in the literature. Cosperpharm employs validated, scalable synthetic routes optimized for industrial production. Batch-specific production records are available upon request.
Storage Conditions
Store Fmoc-Asn-OH in a tightly sealed container at 2–8°C or 2–30°C in a dry, well-ventilated area. Keep the container tightly closed, protected from moisture, and stored away from strong oxidizing agents and strong bases.
Shelf life: Long-term stability is maintained when stored under recommended conditions in a sealed container at appropriate temperature.
Handling precautions: Use in a well-ventilated area. Avoid dust formation. Avoid breathing dust. Avoid contact with skin and eyes. Wear chemical-resistant gloves, safety goggles, and a lab coat. After handling, wash hands thoroughly. This product is for research use only and not for human consumption. Refer to the Safety Data Sheet (SDS) for complete safety information.
Contact Us
Sourcing Fmoc-Asn-OH for your peptide synthesis program, drug discovery project, or academic research should be straightforward. Cosperpharm makes it simple. Reach out to our team today to discuss your requirements, request a quote, or inquire about bulk pricing and custom documentation.
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