Фенилаланил-пролил дикетопиперазин

Description

Phenylalanyl-prolyl diketopiperazine is a cyclic dipeptide closed in a 2,5-diketopiperazine ring of phenylalanine and proline residues. Stereochemically described as cyclo(D-Phe-L-Pro), the systematic name is (3R,8aS)-hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione. Molecular weight 244.29.

Basic Attributes

• CAS No: 26488-24-4
• Molecular Formula: C14H16N2O2
• Melting point: 153–157 °C

Natural spring

• phytotoxin produced by the fungus Alternaria alternata and the actinomycete Streptomyces rochei
• natural product isolated from the polypore Phellinus igniarius

Structural features

The diketopiperazine ring forms stable peptide bonds and at the same time reproduces the conformation of natural peptides—this is the basis for interest in the class as a framework for biologically active molecules. The conformations of the diketopiperazine ring and the phenylalanine side chain are interdependent: the folded conformer is preferred, in which the benzyl group is close to the ring plane.

Connection class

Diketopiperazines are the simplest cyclic peptides that are regularly found among natural compounds and medicinal substances. The cyclic form makes them more resistant to the action of peptidases than linear dipeptides, which explains their prevalence as metabolites of microorganisms and fungi.

Data completeness

The original card contains only the melting point. Density, solubility, spectral and toxicological characteristics, transport codes and GHS classification are not included in it and are not given here. Data for a specific batch is based on the supplier’s certificate of analysis.