3,6-Dimethyl-2,5-Piperazinedione 98% Purity CAS 5625-46-7 High Purity Diketopiperazine Compound for Peptide Research, Pharmaceutical Intermediate, and

Product Overview

3,6-Dimethyl-2,5-piperazinedione, also known as cyclo(L-alanyl-L-alanine) or cyclo(Ala-Ala), is a cyclic dipeptide (diketopiperazine) with the molecular formula C₆H₁₀N₂O₂ and a molecular weight of 142.16 g/mol. This white to off-white crystalline powder is the simplest cyclic dipeptide derived from two alanine residues, serving as a fundamental building block in peptide and diketopiperazine research.

Diketopiperazines represent a class of cyclic dipeptides that exhibit diverse biological activities, including antimicrobial, antitumor, and neuroprotective properties. This compound is widely used as a model system for studying cyclization reactions, conformational analysis of cyclic peptides, and as a precursor for the synthesis of more complex diketopiperazine derivatives with pharmaceutical significance.

Synthetic Process

3,6-Dimethyl-2,5-piperazinedione can be synthesized through the following routes:

• Cyclization of alanine dipeptide: Linear alanine dipeptide (Ala-Ala) is cyclized under acidic or basic conditions, typically using coupling reagents such as DCC or HATU to promote intramolecular amide bond formation.

• Thermal cyclization: Alanine methyl ester is heated under controlled conditions to induce dimerization and cyclization to form the diketopiperazine ring.

• Enzymatic synthesis: Certain proteases and peptidases can catalyze the cyclization of dipeptides to diketopiperazines under mild conditions.

• Purification: The product is purified by recrystallization from ethanol or ethyl acetate.

Mechanism of Action / Application Principles

• Diketopiperazine Research: Serves as a model compound for studying the conformational properties, stability, and biological activities of the diketopiperazine ring system.

• Peptide Synthesis: Used as a building block for the synthesis of more complex cyclic peptides and peptidomimetics.

• Pharmaceutical Intermediate: Serves as a precursor for the synthesis of biologically active diketopiperazine derivatives with potential therapeutic applications.

• Conformational Studies: Used in NMR and computational studies to understand the conformational preferences of cyclic dipeptides.

Quality Specifications

Each batch is accompanied by a Certificate of Analysis (COA).

Packaging & Storage

• Research quantities: 1g, 5g HDPE bottles

• Bulk quantities: 25g HDPE containers

Storage conditions: Store in a cool, dry place in tightly sealed containers. Under recommended conditions, shelf life is 24 months.

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