Boc-Gln-OH

Boc-Gln-OH is a fundamental protected amino acid building block extensively utilized in peptide synthesis, where it serves as the standard reagent for the introduction of L-glutamine residues. The Boc group of Boc-Gln-OH provides robust protection of the α-amino functionality during chain assembly, preventing unwanted side reactions. Boc-Gln-OH is specifically designed for Boc/Bzl chemistry, where repetitive acidolytic deprotection is employed. As a standard building block for introducing glutamine amino-acid residues by Boc solid-phase peptide synthesis (Boc SPPS), Boc-Gln-OH plays a vital role in the synthesis of therapeutic peptides and proteins. Boc-Gln-OH is distinguished by its high optical purity, which is a critical parameter for maintaining chiral integrity during peptide synthesis.

Product Parameters

Synthetic Route

Dissolve L-glutamine (25 g, 0.17 mol) in 300 mL of NaOH aqueous solution (21.9 g, 0.547 mol). Cool the resulting solution to below 10°C, then slowly add a THF solution of Boc anhydride (0.205 mol; 150 mL); note that the reaction is exothermic. Stir the mixture continuously at 25°C for 20 hours. Reaction progress was monitored by TLC using MeOH:CH₂Cl₂ (1:1, containing 0.1% acetic acid) as the developing solvent. Upon completion, separate the organic phase; extract the aqueous phase with hexane (100 mL), acidify it with 2 NHCl to pH 2, and then extract again with ethyl acetate (2 × 250 mL). Combine the organic phases, dry with Na₂SO₄, and evaporate the solvent under vacuum. The resulting viscous oily product was diluted with dichloromethane and further evaporated. After standing for 2–3 days, crystallize the product in hexane to yield N-(Boc)-L-glutamine (1) (37.5 g, yield 89%) as a colorless solid. The product was characterized by ¹H NMR (DMSO, 300 MHz) and ESI-MS (m/z: 269 [M + Na⁺]).

FAQ

A: Boc-Gln-OH (Nα-Boc-L-glutamine, CAS 13726-85-7) is a protected derivative of L-glutamine featuring a tert-butoxycarbonyl (Boc) group protecting the α-amino functionality.

Q2: What are the primary applications of Boc-Gln-OH?

A: Boc-Gln-OH is primarily used as a protected amino acid building block in peptide synthesis, particularly in Boc solid-phase peptide synthesis (Boc SPPS). It is employed in the synthesis of therapeutic peptides including human β-endorphin analogs.

Product Quality Assurance

Thorough analytical characterization. Each batch undergoes multi-technique analytical release testing: HPLC purity (≥98% with full chromatographic traceability), melting point verification (113–116 °C, dec.), optical rotation confirmation, appearance verification, and residual solvent analysis.

Full batch traceability with retention samples. From raw material procurement through Boc protection, work-up, purification, and final packaging, every step is fully documented and traceable. Each batch receives a unique lot number with sufficient retention samples maintained.

Stability monitoring program. Cosperpharm conducts ongoing stability studies under recommended storage conditions: long-term storage at –20 °C (3 years) and at 4 °C (2 years). Stability summaries are available to support customer regulatory and research submissions.

Documentation ready for regulatory and research 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. Custom quality agreements and additional characterization data are available upon request.

Customer‑initiated quality audits. Qualified customers are welcome to audit Cosperpharm‘s manufacturing, quality control, and documentation facilities.

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