Boc-D-Pro-OH

Boc-D-Pro-OH is a standard building block for the introduction of D-proline amino acid residues in Boc-based solid-phase peptide synthesis (SPPS). The unique cyclic structure of proline — preserved in Boc-D-Pro-OH — imposes significant conformational constraints on peptide backbones, making proline-containing peptides valuable tools for studying protein structure-function relationships and for developing conformationally restricted peptide therapeutics. As a key building block in the synthesis of peptides and biologically active compounds, Boc-D-Pro-OH enables medicinal chemists to explore the impact of D-proline stereochemistry on peptide conformation, receptor binding, and pharmacokinetic properties. The robust Boc protective group in Boc-D-Pro-OH is crucial for facilitating selective reactions and improving the yield of target molecules during peptide synthesis. In biochemical research, Boc-D-Pro-OH serves as a precursor for the synthesis of optically pure peptides and biologically active compounds, with its rigid pyrrolidine ring contributing to the conformational stability and target selectivity of the final products. The D-configuration of Boc-D-Pro-OH also provides enhanced proteolytic stability compared to L-proline-containing analogs, addressing one of the major challenges in peptide drug development.

 

 Product Parameters

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Parameter	Specification
Product Name	Boc-D-Pro-OH
CAS Number	37784-17-1
Molecular Formula	C₁₀H₁₇NO₄
Molecular Weight	215.25 g/mol
Appearance	White to off-white microcrystalline powder
Melting Point	134–137 °C (lit.)
Boiling Point	355.52 °C at 760 mmHg
Density	1.1835 g/cm³
Storage Condition	2–8 °C

 

Application

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Boc-D-Pro-OH is used as a biochemical reagent and serves as a protective monomer for amino acids.

 

Synthetic Route

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At room temperature, NaHCO₃ (182.4 g, 2.5 equivalents) and water (800 mL, 8 volumes) were added to a stirred solution of D-proline (100 g, 868.58 mmol) in dioxane (400 mL, 8 volumes), and the mixture was stirred for approximately 30 minutes. The reaction mixture was cooled to 0–5 °C, followed by slow addition of diisopropyl carbonate (Boc₂O) (224.26 g, 1.2 equivalents), and continued stirring at 0–5 °C for 1 hour. The mixture was then gradually warmed to room temperature and stirred overnight (12 hours). Reaction progress was monitored by thin-layer chromatography (TLC). Upon completion, the dioxane solvent was evaporated under reduced pressure. The aqueous phase was acidified to pH 2–3 with 4 NHCl solution at 0–5 °C. The aqueous phase was extracted with ethyl acetate (4 × 200 mL), the organic layers were combined, washed with water, and dried with anhydrous Na₂SO₄. The organic layer was concentrated under reduced pressure to yield a white solid product. This solid was added to heptane (200 mL) and stirred at room temperature for 2 hours. The resulting solid was filtered, collected, and vacuum-dried at 45–50 °C to obtain the target compound.

 

Product Quality Assurance

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Cosperpharm has established a comprehensive quality assurance system for Boc-D-Pro-OH that meets the rigorous expectations of both peptide synthesis intermediate manufacturing and reference standard applications:

 

Thorough analytical characterization. Each batch undergoes multi-technique analytical release testing: HPLC purity (≥99.0% industrial grade; ≥95.0% reference standard grade, with full chromatographic traceability), optical rotation verification ([α]²⁰/D +61±2°, c=2% in acetic acid), melting point verification (133–137 °C), appearance verification (white to off-white microcrystalline powder), water content determination (Karl Fischer <0.5%), residual solvent analysis (GC), and where applicable, ¹H NMR and MS confirmation of molecular identity.

 

Full batch traceability with retention samples. From raw material procurement (D-proline from qualified suppliers) through Boc protection, purification, and final packaging, every step is fully documented and traceable. Each batch receives a unique lot number with sufficient retention samples maintained in accordance with Cosperpharm quality procedures.

 

Stability monitoring program. Cosperpharm conducts ongoing stability studies under recommended storage conditions: long-term storage at –20 °C under inert atmosphere, with accelerated stability studies (40 °C / 75% RH) conducted on representative batches. Stability summaries are updated regularly, with full data packages available to support customer regulatory submissions. Shelf life: 3 years at –20 °C; 2 years at 4 °C.

 

Documentation ready for regulatory submission. Every shipment includes a Certificate of Analysis (COA) with batch-specific purity and characterization data, a Material Safety Data Sheet (SDS), and customs documentation for international delivery. For customers preparing regulatory filings for peptide-based therapeutics, Cosperpharm provides DMF-ready documentation packages, method validation reports, stability data, and custom quality agreements upon request.

 

Customer-initiated quality audits. Qualified customers are welcome to audit Cosperpharm's manufacturing, quality control, and documentation facilities. Please contact our regulatory team to schedule an audit. ISO compliance documentation is available upon request.

 

Contact Us

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Ready to secure Boc-D-Pro-OH for your peptide synthesis campaign or medicinal chemistry program? Cosperpharm delivers high-quality Boc-protected amino acids with the documentation and supply reliability you need. Contact our team today — we're here to help you succeed, from R&D to commercial manufacturing.