Boc-L-Pyroglutamic acid ethyl ester, with the CAS number 144978-12-1, is a protected cyclic amino acid derivative, also known as Boc-L-Pyr-Oet or Ethyl (S)-1-(tert-butoxycarbonyl)-5-oxopyrrolidine-2-carboxylate. Its molecular formula is C₁₂H₁₉NO₅, and the molecular weight is 257.28 g/mol. This compound is derived from L-glutamic acid via intramolecular cyclization to form a pyroglutamic acid (L-Pyr) core, with an amino group protected by a Boc (tert-butoxycarbonyl) group and a carboxyl group esterified as an ethyl ester. Its unique structure, combining a rigid cyclic scaffold with orthogonal protecting groups, makes it a valuable building block in peptide synthesis, drug discovery, and biochemical research.
Physically, it appears as a white to off-white crystalline powder or solid. It has a melting point in the range of 60-65°C and exhibits good thermal stability under normal storage conditions. Chemically, it is sparingly soluble in water but readily soluble in common organic solvents such as dichloromethane (DCM), dimethylformamide (DMF), tetrahydrofuran (THF), and ethyl acetate, making it highly suitable for solid-phase peptide synthesis (SPPS) and solution-phase organic synthesis. The compound is optically active, with a specific rotation [α]²⁰/D typically ranging from-10.0° to -14.0° (in methanol, c=1), reflecting its L-configuration. It has low hygroscopicity and remains stable under neutral and weakly acidic conditions, but may undergo deprotection under strong acidic conditions (e.g., trifluoroacetic acid, TFA).
Its primary application lies in the synthesis of peptides and peptidomimetics. The Boc protecting group is cleavable under acidic conditions, making it compatible with standard SPPS protocols. The pyroglutamic acid (L-Pyr) moiety is a cyclic amino acid that can constrain peptide backbone conformations, improving the metabolic stability, cell permeability, and binding affinity of the resulting peptide drugs. It is often used to introduce N-terminal cyclic structures or mimic biologically active peptide conformations.
In pharmaceutical research, it is extensively used to develop novel therapeutics targeting various diseases, includingneurodegenerative disorders,antimicrobial agents, and anticancer drugs. For example, incorporating L-Pyr into peptide sequences can enhance their resistance to enzymatic degradation and improve their ability to cross biological membranes. Additionally, it serves as a key intermediate in the synthesis of complex organic molecules and chiral ligands for asymmetric catalysis.
Safety-wise, this compound is considered stable and non-toxic under normal handling conditions. However, as with all fine chemicals, proper precautions should be taken. It should be stored in a sealed, cool, and dry environment at room temperature, away from strong acids, strong oxidizing agents, and high temperatures to prevent premature deprotection or degradation.
In summary, Boc-L-Pyroglutamic acid ethyl ester is an indispensable tool in modern medicinal chemistry and peptide science, enabling the construction of highly structured and biologically active molecules with precise control over stereochemistry and conformation.
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