Fmoc-Dab(Boc)-OH

Fmoc-Dab(Boc)-OH is a standard building block for the introduction of 2,4-diaminobutyric acid (Dab) residues into peptides via Fmoc solid‑phase peptide synthesis (SPPS). The orthogonal protection—base‑labile Fmoc on the α‑amine and acid‑labile Boc on the γ‑amine—enables sequential deprotection and selective functionalization, making Fmoc-Dab(Boc)-OH particularly valuable for the synthesis of branched peptides, peptide dendrimers, and cyclic peptides where the side‑chain amine serves as an additional point of attachment. As a non‑proteinogenic amino acid, Fmoc-Dab(Boc)-OH expands the chemical diversity accessible in peptide libraries beyond the canonical 20 proteinogenic amino acids. The Dab side chain—shorter than lysine by two methylene units—introduces a basic amine with distinct steric and electronic properties. In drug discovery contexts, Fmoc-Dab(Boc)-OH has been utilized in the synthesis of polymyxin mimetic peptides, antimicrobial agents, and cyclic peptide therapeutics. For quality control applications, Fmoc-Dab(Boc)-OH serves as an analytical reference standard for HPLC method development and impurity profiling in peptide API manufacturing.

Product Parameters

Synthetic Route

The general procedure for synthesizing N-fluoromethoxycarbonyl-N'-tert-butoxycarbonyl-L-2,4-diaminobutyric acid from di-tert-butyl dicarbonate and Fmoc-L-2,4-diaminobutyric acid is as follows: 50 g (146.8 mmol) of Fmoc-L-2,4-diaminobutyric acid was suspended in a mixture of 700 mL of acetone and water (volume ratio 1:1), and 38.4 g (176 mmol) of di-tert-butyl dicarbonate was slowly added under 0°C. The reaction mixture was then adjusted to pH 7.5–8 using 0.5 M NaOH solution. After 4 hours of reaction, 56 g of the desired product was obtained with a yield of 86.62% and HPLC purity of 99.4%.

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Storage Conditions

Store Fmoc-Dab(Boc)-OH in a tightly sealed container, protected from light and moisture. For short‑term storage (up to 12 months), store at 2–8 °C. For long‑term storage exceeding 12 months, store at –20 °C under inert atmosphere (nitrogen or argon). The compound is stable under recommended storage conditions.

Shelf life: 3 years when stored at –20 °C in a sealed container under inert atmosphere; 2 years when stored at 4 °C. Accelerated stability data and long‑term stability summaries are available upon request.

Handling precautions: Avoid generating dust. Use in a fume hood. Wear chemical‑resistant gloves (tested against EN 374 or equivalent), safety goggles, and a lab coat. After handling, wash hands thoroughly. Contaminated clothing should be removed and washed before reuse. The compound is for research use only and is not intended for diagnostic or therapeutic procedures.

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Need a reliable source of Fmoc-Dab(Boc)-OH for your complex peptide synthesis project or regulatory filing? Cosperpharm handles the quality control, documentation, and supply chain logistics—contact us today to discuss your requirements.