Fmoc-D-Leu-OH

Fmoc-D-Leu-OH is a standard building block for the incorporation of D-leucine residues into peptides via Fmoc solid-phase peptide synthesis. D-Leucine—the non-natural enantiomer of leucine—resists cleavage by proteolytic enzymes that recognize L-amino acids, making Fmoc-D-Leu-OH a strategic intermediate in the development of metabolically stable therapeutic peptides. As a D-enantiomer amino acid derivative, Fmoc-D-Leu-OH also serves as a valuable research tool for structure-activity relationship studies exploring the effects of stereochemical inversion on peptide bioactivity, receptor binding selectivity, and plasma stability. In drug development applications, Fmoc-D-Leu-OH has been utilized in the synthesis of dipeptidyl peptidase-4 (DPP-4) inhibitors for diabetes treatment. The Fmoc group in Fmoc-D-Leu-OH offers convenient spectrophotometric monitoring during automated coupling cycles, and the free carboxylic acid provides the reactive site for chain elongation. When used in solid-phase peptide synthesis, Fmoc-D-Leu-OH helps researchers construct specific amino acid sequences for therapeutic purposes while maintaining high purity levels.

Product Parameters

Why Cosperpharm? – Our Competitive Advantages

Synthetic Route

In the presence of a base, 9-fluoromethoxycarbonyl chloride reacts with leucine to yield FMOC-D-leucine. This method is characterized by simple operation, mild reaction conditions, high yield, and broad applicability for the preparation of FMOC-D-leucine. The synthetic reaction equation for FMOC-D-leucine is shown in the figure below:

FAQ

Q1: What is the difference between Fmoc-D-Leu-OH and Fmoc-L-Leu-OH?

A: Fmoc-D-Leu-OH contains D-leucine, the non‑natural enantiomer of leucine, whereas Fmoc-L-Leu-OH contains the naturally occurring L‑leucine. The D‑enantiomer confers resistance to proteolytic degradation when incorporated into peptides, making it valuable for therapeutic peptide design. Peptides containing D‑amino acids also exhibit altered conformational preferences and binding characteristics compared to their all‑L counterparts.

Q2: Is Fmoc-D-Leu-OH soluble in water?

A: No. Fmoc-D-Leu-OH is insoluble in water due to the hydrophobic leucine side chain and the aromatic Fmoc group. It is soluble in organic solvents such as DMSO (≥35.3 mg/mL), ethanol (≥94 mg/mL), DMF, and dichloromethane. For SPPS applications, it is typically dissolved in DMF or NMP.

Contact Us

Getting Fmoc-D-Leu-OH for your peptide synthesis campaign, drug discovery program, or reference standard needs should be efficient and straightforward. Cosperpharm handles the sourcing, quality control, and logistics so you can focus on the science.