N-Boc-O-Benzyl-D-serine

Sinonimi: Boc-D-Ser(Bzl)-OH, N-tert-Butoxycarbonyl-O-benzyl-D-serine, (R)-2-(Boc-amino)-3-(benzyloxy)propanoic acid, Boc-O-benzyl-D-serine, N-Boc-O-benzyl-D-serine

N-Boc-O-Benzyl-D-serine is a protected derivative of the non-proteinogenic D-serine, featuring orthogonal protecting groups that make it a staple in modern peptide synthesis. The tert-butoxycarbonyl (Boc) group shields the α-amino function, while the benzyl (Bzl) ether masks the side-chain hydroxyl, allowing selective deprotection and further elaboration. This compound is the D-enantiomer of the widely used L-series building block and is valued for introducing D-serine residues into peptides to modulate conformation, stability, and biological activity.

In the realm of medicinal chemistry, D-amino acid residues are often incorporated to improve metabolic stability and binding affinity. N-Boc-O-Benzyl-D-serine serves as a key intermediate for producing D-serine-containing peptides, which are explored in enzyme inhibitors, receptor ligands, and antimicrobial agents. The benzyl group is particularly useful because it can be removed by catalytic hydrogenation or strong acids without affecting the Boc group, offering flexibility in synthetic routes. Its crystalline nature and high enantiomeric purity make it a reliable choice for solid-phase and solution-phase peptide synthesis.

Beyond peptide chemistry, this compound finds application in the preparation of chiral catalysts and as a building block for unnatural amino acids. The D-configuration is critical for interactions with biological targets that exhibit stereospecificity, such as enzymes involved in bacterial cell wall synthesis. As research into D-amino acid-containing therapeutics grows, the demand for high-quality protected D-serine derivatives continues to rise. LyvBio supplies N-Boc-O-Benzyl-D-serine with rigorous quality control, ensuring consistent performance in your synthetic sequences.

Funzione

• Peptide synthesis building block: Introduces D-serine residues with orthogonal protection for Boc-SPPS or solution-phase synthesis.
• Chiral intermediate: Enables the synthesis of enantiomerically pure D-serine derivatives and unnatural amino acids.
• Hydroxyl protection: Benzyl ether prevents side reactions during chain elongation and can be selectively removed.
• Amino protection: Boc group is stable under basic and hydrogenolytic conditions, allowing selective deprotection.
• Medicinal chemistry tool: Used to optimize peptide stability, bioavailability, and target affinity in drug discovery.

Fonte e standardizzazione

• Fonte: Synthetic, derived from D-serine via sequential protection steps.
• Manufacturing process: Boc protection of D-serine, followed by benzylation of the hydroxyl group; purified by crystallization.
• Standardizzazione: ≥98.0% purity by HPLC; enantiomeric excess (ee) ≥99.5%.
• Moduli: White to off-white crystalline powder.
• Applicazioni: Peptide synthesis, pharmaceutical intermediates, chiral building blocks, research and development.

Caratteristiche tecniche

Documentazione e forniture

• Capacità mensile: 500 kg
• Tempi di consegna: 3-5 business days (stock items)
• Documentazione: COA, MSDS, TDS, and analytical chromatograms available upon request
• Confezionamento: 25 kg fiber drum with double polyethylene liners; custom packaging available
• Archiviazione: Store at 2-8 °C, protected from light and moisture

Richiesta di preventivo

• LyvBio S.r.l. — E-mail: info@lyvbio.com