Sigma-Aldrich™ Fmoc-Glu(OtBu)-OH, ≥98.0% (HPLC), for peptide synthesis

Fmoc-Glu(OtBu)-OH (Fmoc-L-glutamic acid 5-tert-butyl ester) is a high-purity, protected amino acid derivative widely used in solid-phase peptide synthesis (SPPS) and bioconjugation chemistry. This reagent features:

• Fmoc (9-fluorenylmethyloxycarbonyl) protection at the N-terminal for selective deprotection during peptide elongation.
• tBu (tert-butyl) protection on the γ-carboxyl group, preventing unwanted side reactions and ensuring controlled peptide synthesis.

This reagent is a key building block in peptide synthesis, drug discovery, and biopolymer engineering, providing structural flexibility and chemical stability for peptide modifications.

Key Features & Benefits

✔ High Purity (≥98.0%) – Ensures reliable and reproducible peptide synthesis.

✔ Fmoc & tBu Protection – Provides selective deprotection, enabling controlled peptide assembly.

✔ Ideal for Solid-Phase Peptide Synthesis (SPPS) – Prevents side reactions while enabling efficient peptide elongation.

✔ Versatile Applications – Used in protein engineering, drug development, and biochemical studies.

✔ Stable & Well-Characterized – Optical activity ([α]²⁰/D -5.0±2.0°), HPLC assay (≥98.0%), and low impurity levels (~4% water content) ensure high-quality performance.

Chemical Properties & Identifiers

Applications

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

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

🔹 Bioconjugation & Protein Engineering – Facilitates biomolecule modifications and bioactive compound synthesis.

🔹 Bioorganic Chemistry & Materials Science – Used in biopolymer design and functional material synthesis.

✔ Reported Applications Include:

1️⃣ Ligand in the Synthesis of cis-Substituted Cyclopropane Carboxylic Acids – Used in C-H activation of cyclopropane carboxamides via Pd-catalyzed reactions.

2️⃣ Linker in Multi-Small Molecule-Conjugated PTX (Paclitaxel) Derivatives – Applied in drug conjugation strategies for targeted therapy.

3️⃣ Stapled α-Helical Peptides – Used in stapled peptide design for enhanced bioactivity and stability.

4️⃣ Peptide C-Terminal Thioesters – Employed in native chemical ligation (NCL) for protein semi-synthesis.

Storage & Handling

📦 Storage Conditions:

• Store at 2-8°C in a dry, tightly sealed container.
• Keep away from oxidizing agents and moisture to maintain stability.

⚠ Handling Precautions:

• Use in a well-ventilated area.
• Wear PPE – gloves, lab coat, and safety goggles.
• Avoid exposure to moisture and direct sunlight.

General References & Research Citations

1️⃣ Ligand in the Synthesis of cis-Substituted Cyclopropane Carboxylic Acids – Org. Lett., 2013, 15(9), 2179-2182.

2️⃣ Linker in Multi-Small Molecule-Conjugated PTX (Paclitaxel) Derivatives – J. Med. Chem., 2018, 61(11), 4941-4954.

3️⃣ Stapled α-Helical Peptides – Nature Chemistry, 2014, 6(7), 614-622.

4️⃣ Peptide C-Terminal Thioesters – J. Am. Chem. Soc., 2012, 134(42), 17714-17721.

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-Glu(OtBu)-OH (≥98.0%) is a high-purity, selectively protected amino acid essential for solid-phase peptide synthesis (SPPS), pharmaceutical research, and biochemical studies. Its Fmoc and tBu protection enable precise deprotection steps, making it ideal for controlled peptide assembly, protein engineering, and biomedical applications.