5654-86-4

Basic information

• Product Name: 3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• Synonyms: 2,3,6,7,8,8a-Hexahydro-3-isobutylpyrrolo[1,2-a]pyrazine-1,4-dione;3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;6,7,8,8a-Tetrahydro-3-isobutylpyrrolo[1,2-a]pyrazine-1,4(2H,3H)-dione;Octahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(leucyloprolyl);Pyrrolo(1,2-A)pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-;cyclic dipeptide with proline
• CAS NO: 5654-86-4
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.2728
• Mol File: 5654-86-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 163-165 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 427.6°Cat760mmHg
• Flash Point: 212.4°C
• Appearance: /
• Density: 1.14g/cm³
• PKA: 13.27±0.40(Predicted)
• CAS DataBase Reference: 3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(5654-86-4)
• EPA Substance Registry System: 3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(5654-86-4)

Safety Data

• Hazardous Substances Data: 5654-86-4(Hazardous Substances Data)

Usage

General Description

3-Isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is a chemical compound with a complex molecular structure. It is commonly referred to as PDP or pentetrazol, and is used in the synthesis of pharmaceuticals and organic compounds. PDP is a heterocyclic compound, containing both nitrogen and oxygen atoms within its ring structure. It is known for its potential as a central nervous system stimulant and has been studied for its possible applications in the treatment of neurological disorders. It also has potential use as a flavoring agent in food products. Because of its unique structure and potential therapeutic properties, PDP is a subject of ongoing research in the fields of chemistry and pharmacology.

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 96163-72-3 ethyl proline hydrochloride 
• 116939-86-7 ((benzyloxy)carbonyl)-L-leucyl-L-proline 
• 1380332-79-5 cyclo(Z-L-Leu-D-Pro) 
• 1380332-87-5 Cbz-(L)-leucyl-(D)-prolyl benzotriazole 
• 1380332-71-7 Cbz-(L)-leucyl-(L)-prolyl benzotriazole 
• 2018-66-8 Z-Leu-OH 
• 75188-89-5 L-prolyl-L-leucylglycylglycine 
• 52899-07-7 L-prolyl-L-leucine 
• 2899-43-6 DL-leucine ethyl ester 

Downstream Products

• 61-90-5 L-leucine 
• 147-85-3 L-proline 
• 1072102-31-8 (8aR)-3c-isobutyl-(8ar)-octahydro-pyrrolo[1,2-a]pyrazine 

Relevant articles and documents

Molecular capture and conformational change of diketopiperazines containing proline residues by epigallocatechin-3-O-gallate in water

The addition of an aqueous solution of diketopiperazine cyclo(Pro-Xxx) (Xxx: amino acid residue) to an aqueous solution of (?)-epigallocatechin-3-O-gallate (EGCg) led to precipitation of the complex of EGCg and cyclo(Pro-Xxx). The molecular capture abilities of cyclo(Pro-Xxx) using EGCg were evaluated by the ratio of the amount of cyclo(Pro-Xxx) included in the precipitates of the complex with EGCg to that of the total cyclo(Pro-Xxx) used. Stronger hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg, and formed a complex, their conformation was maintained in the hydrophobic space. Based on nuclear Overhauser effect (NOE) measurement, the 3-position methyl group of cyclo(D-Pro-L-Ala) in D2O was axial, whereas that of cyclo(L-Pro-L-Ala) was equatorial. When cyclo(D-Pro-L-Ala) was taken into the hydrophobic space of EGCg and formed a 2:2 complex, its 3-position methyl group changed from the axial position to the equatorial position due to steric hindrance by EGCg.

AGRICULTURAL CHEMICAL CONTAINING 2,5-DIKETOPIPERAZINE DERIVATIVE AS ACTIVE INGREDIENT

Disclosed herein is an agricultural agent containing a 2,5-diketopiperazine derivative capable of controlling plant diseases and promoting plant growth or an agriculturally acceptable salt thereof as an active ingredient.

Model studies of competing hydrolysis and epimerization of some tetrapeptides of interest in amino acid racemization studies in geochronology

The processes of epimerization of individual peptide units in proteins and the concurrent cleavage of peptide bonds are modelled by heating some tetrapeptide and tetrapeptide derivatives to 148.5 deg C in pH 6.8 phosphate buffer.An excess of D-proline was observed during the heating of L-propyl-L-leucylglycylglycine.The D/L ratio of proline attains a maximum value of 2.1 after 90 minutes.The excess D-proline is attributed to the formation of a 2.3:1 mixture of diketopiperazines cyclo-(D-propyl-L-leucyl) and cyclo-(L-prolyl-L-leucyl).These two species account for most of the leucine and proline in the final mixture after the tetrapeptide is no longer detectable.Only small amounts of prolylleucine can be detcected after 50 hours.It is suggested that the above tetrapeptide undergoes internal aminolysis.Leucine in the tetrapeptide glycyl-L-leucylglycylglycine racemizes three times faster than in L-propyl-L-leucylglycylglycine.This demonstrates that an amino acid residue in a peptide chain does have an effect upon the rate of epimerization of a neighbouring peptide residue.A discussion of the geochemical implications of the results is included.