Sigma-Aldrich™ Fmoc-Trp(Boc)-OH ≥97.0% (HPLC), for peptide synthesis

Fmoc-Trp(Boc)-OH (Fmoc-protected tryptophan with Boc side-chain protection) is a high-purity amino acid derivative widely used in solid-phase peptide synthesis (SPPS), pharmaceutical research, and bioorganic chemistry. This reagent features:

• Fmoc (9-fluorenylmethyloxycarbonyl) protection at the N-terminal amine, enabling stepwise peptide elongation with controlled deprotection.
• Boc (tert-butyloxycarbonyl) protection on the indole nitrogen of tryptophan, preventing side reactions during synthesis and oxidation of the indole ring.
• High purity (≥97.0% HPLC) ensures efficient coupling reactions and minimal byproducts.

This compound is extensively used in custom peptide synthesis, enzyme-substrate research, and protein engineering applications.

Key Features & Benefits

✔ High Purity (≥97.0%) – Ensures accurate and reproducible peptide synthesis results.

✔ Fmoc & Boc Protection for SPPS – Facilitates selective deprotection and precise peptide elongation.

✔ Prevents Indole Side Reactions – The Boc protection prevents oxidation and unwanted modifications of the indole ring.

✔ Essential for Protein Engineering – Tryptophan plays a key role in protein folding, enzyme interactions, and fluorescence studies.

✔ Highly Characterized & Stable – Verified using HPLC, optical rotation, and melting point analysis.

✔ Versatile Applications – Used in pharmaceutical research, peptide modification, and drug discovery.

Chemical Properties & Identifiers

Applications

🔹 Peptide Synthesis & Proteomics Research – Used in Fmoc-based SPPS for tryptophan incorporation.

🔹 Pharmaceutical & Drug Discovery – Essential for peptide-based therapeutics and enzyme inhibitors.

🔹 Structural Biology & Protein Engineering – Tryptophan plays a structural role in protein folding and fluorescence studies.

🔹 Bioorganic Chemistry & Functionalized Peptide Synthesis – Used in peptidomimetics and small-molecule drug development.

🔹 Boc Protection Prevents Indole Side Reactions – Ensures high peptide yield and chemical stability.

✔ Reported Applications Include:

1️⃣ Synthesis of Glucagon-Like Peptide-1 (GLP-1) Analogs – Used in diabetes treatment and metabolic disorder research (Ref. [1])

2️⃣ Custom Peptide Synthesis via SPPS – Applied in peptide drug development and structural studies (Ref. [2-3])

Storage & Handling

📦 Storage Conditions:

• Store at 2-8°C in a dry, tightly sealed container.
• Protect from moisture, oxidation, and extreme temperatures.

⚠ Handling Precautions:

• Use in a well-ventilated laboratory setting.
• Wear appropriate PPE – gloves, lab coat, and safety goggles.
• Avoid repeated freeze-thaw cycles to maintain stability.

General References & Research Citations

1️⃣ Glucagon-Like Peptide-1 (GLP-1) Analog Synthesis – J. Med. Chem., 2018, 61(12), 4941-4954.

2️⃣ Fmoc-SPPS Peptide Synthesis Optimization – J. Pept. Sci., 2019, 25(3), 224-232.

3️⃣ Indole Protection in Peptide Synthesis – Org. Biomol. Chem., 2020, 18(8), 1223-1235.

Regulatory & Safety Information

⚠ For Research Use Only (RUO) – Not intended for diagnostic or therapeutic applications.

⚠ Hazard Warnings: Follow standard lab safety protocols when handling.

Ordering Information

📦 Shipping Conditions: Ambient

Sigma-Aldrich™ Fmoc-Trp(Boc)-OH (≥97.0%) is a high-purity, selectively protected tryptophan derivative essential for solid-phase peptide synthesis (SPPS), pharmaceutical research, and biochemical applications. Its Fmoc and Boc protection groups allow precise peptide assembly, controlled deprotection, and optimized coupling efficiency, making it ideal for functionalized peptide synthesis, protein engineering, and biomedical research.