Boc-L-Pyroglutamic acid methyl ester

Boc-L-Pyroglutamic acid methyl ester

CAS No.: 108963-96-8

It is an important chiral amino acid derivative, with core applications concentrated in three major fields: peptide drug synthesis, pharmaceutical intermediates, and cosmetic ingredients.

1. Pharmaceutical & Peptide Synthesis (Core Application)
Peptide Synthesis Protecting Agent: The Boc (tert-butoxycarbonyl) group in the molecule is a classic amino-protecting group, which prevents side reactions of the amino group in Solid-Phase Peptide Synthesis (SPPS), enabling the precise construction of complex peptide chains.
Chiral Building Block: Its unique cyclic structure and fixed L-chirality make it a key chiral intermediate for the synthesis of anti-HIV, anti-tumor, and neurological drugs.
Drug Molecular Modification: Used to improve the solubility, stability, and pharmacokinetic (absorption/distribution/metabolism) properties of drug candidates.
Targeted Drug Conjugation: Serves as a linker in the research and development of targeted therapeutics such as Antibody-Drug Conjugates (ADCs).

2. Cosmetics & Personal Care
High-Efficiency Moisturizer: Its derivatives (e.g., sodium pyroglutamate) exhibit superior moisturizing power compared to glycerin and sorbitol. They are non-toxic and non-irritating, making them ideal for high-end skin and hair care products.
Skin-Whitening Active Agent: Inhibits tyrosinase activity, preventing the deposition of melanin (melanoid) to achieve skin brightening and lightening effects.

3. General Organic Synthesis
Versatile Intermediate: Combines an amino-protecting group, a methyl esterified carboxyl group, and a pyrrolidone ring. It undergoes diverse reactions including hydrolysis, reduction, and coupling, and is used to construct complex heterocyclic compounds.
Chiral Catalyst/Ligand: Its chiral backbone can be used to synthesize ligands for asymmetric catalysis, controlling the stereoselectivity of products.

Summary of Core Advantages:
Dual Protection: Boc (amino) + methyl ester (carboxyl), offering controllable reaction sites and strong compatibility.
Chiral Purity: Natural L-configuration, meeting the stereospecificity requirements of pharmaceuticals and peptides.
High Stability: Exists as a white solid at room temperature, facilitating easy storage and purification.