(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, CAS No. 2873-36-1

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2873-36-1

Catalog No. EBD3321168

CAS 2873-36-1

Name (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

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Basic Information

Synonyms: (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (3S-trans)-hexahydro-3-isobutylpyrrolo[1,2-a]pyrazine-1,4-dione Cyclo(-Leu-Pro) Pyrrolo(1,2-a)pyrazine-1,4-dione,hexahydro-3-isobutyl-,stereoisomer 5-24-07-00347(BeilsteinHandbookReference) BRN0085716 Cyclo-L-leu-L-pro GancidinW (3S-trans)-Hexahydro-3-isobutylpyrrolo(1,2-a)pyrazine-1,4-dione Pyrrolo(1,2-a)pyrazine-1,4-dione,hexahydro-3-(2-methylpropyl)-,(3S-trans)- 3-(2-methylpropyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (3S,8aS)-3-(2-methylpropyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Molecular Formula: C11H18N2O2

Molecular Weight: 210.27

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

Cyclo(L-prolyl-L-leucyl) is a cyclic dipeptide, specifically a diketopiperazine (DKP), formed from the amino acids L-proline and L-leucine. It is also known as cyclo(Pro-Leu) or (3S,8aS)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione. This compound is a member of the 2,5-diketopiperazine family, a class of molecules known for their structural rigidity and diverse biological activities. This cyclic dipeptide serves as a versatile scaffold in medicinal chemistry and peptide research. It is frequently utilized as a constrained peptidomimetic building block to study peptide conformation and to design novel bioactive compounds. DKPs like cyclo(Pro-Leu) are found in various natural products and are known to exhibit a range of pharmacological properties, including antimicrobial, antifungal, and anticancer activities, making them valuable intermediates in drug discovery programs. The compound is also of interest in chemical biology for probing protein-protein interactions and enzyme inhibition due to its ability to mimic peptide turn structures. Its synthesis and derivatization are active areas of research for developing new therapeutic agents and biochemical tools.

Physical Properties

Boiling Point: 427.6°Cat760mmHg

Flash Point: 212.4°C

Density: 1.14g/cm3