Fmoc-D-Phe-OH

Fmoc-D-Phe-OH is the standard building block for the incorporation of D‑phenylalanine residues into custom peptides via Fmoc solid‑phase peptide synthesis (Fmoc SPPS). The Fmoc group in Fmoc-D-Phe-OH provides robust N‑terminal protection during chain assembly, ensuring that each amino acid coupling proceeds in the desired direction without premature termination or branching. The D‑configuration of the amino acid renders Fmoc-D-Phe-OH particularly useful for synthesizing protease‑resistant peptides, including peptide hormones, antimicrobial peptides, and enzyme inhibitors, where the unnatural backbone increases metabolic stability in biological systems. Additionally, Fmoc-D-Phe-OH serves as a versatile intermediate in the preparation of chiral building blocks for pharmaceutical compounds, peptidomimetics, and stereochemically defined drug candidates.

Product Parameters

Why Cosperpharm? – Our Competitive Advantages

Product Advantages

1. Standard Building Block for Fmoc SPPS

Fmoc-D-Phe-OH is the industry‑standard building block for introducing D‑phenylalanine residues into peptide sequences via Fmoc solid‑phase peptide synthesis. The Fmoc protecting group is stable to acid, orthogonal to side‑chain protecting groups (t‑Bu, Boc, Pbf, Trt), and cleaved rapidly under mild basic conditions (20% piperidine in DMF) without affecting the growing peptide chain or resin linkage.

2. Enhanced Proteolytic Stability

The D‑enantiomer configuration confers exceptional resistance to enzymatic hydrolysis by endogenous proteases, making Fmoc-D-Phe-OH ideal for synthesizing long‑acting peptide therapeutics, antimicrobial peptides, and enzyme‑resistant analogs of endogenous peptide hormones.

3. High Purity and Low Dipeptide Content

Cosperpharm supplies Fmoc-D-Phe-OH with low levels of dipeptide, free‑amino acids, and acetic acid impurities that can interfere with coupling efficiency and produce truncated sequences during automated peptide synthesis.

4. Versatile Scaffold for Peptidomimetics

The rigid aromatic side chain of Fmoc-D-Phe-OH can be utilized in the design of constrained peptidomimetics, β‑hairpin inducers, and β‑turn mimics. The D‑configuration introduces unique backbone conformation that can enhance target binding affinity and selectivity.

5. Dual‑Use: Peptide Synthesis and Impurity Reference Standard

Cosperpharm supplies Fmoc-D-Phe-OH at two quality levels: industrial grade (≥98% HPLC) for use as a synthetic building block in peptide API manufacturing; and reference standard grade (≥99.5% chiral HPLC with full characterization) for use as an analytical standard in enantiomeric purity testing of Fmoc‑L‑phenylalanine batches.

Synthetic Route

For the synthesis of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyridinopyrimidin-4-one, the conventional approach starts with 2-amino-3-benzoylopyridine, which undergoes a one-step condensation reaction in the presence of phosphine trichloride to yield the target product with the hydroxyl group protected by a benzyl group; subsequent removal of the benzyl group under palladium-carbon hydrogenation conditions yields the desired compound. It should be noted that during palladium-carbon hydrogenation, a pressure of one atmosphere is sufficient for hydrogen gas, and heating conditions can yield better reaction outcomes.

Contact us

Ready to secure Fmoc-D-Phe-OH for your peptide synthesis campaign or analytical program? Reach out to Cosperpharm today for a competitive quote and reliable supply.