36238-64-9

Usage

Chemical Properties

White powder

Upstream product

• 162441-99-8 N-<2(R)-bromopropanoyl>-(2S)-proline methyl ester 
• 129474-02-8 Cbz-D-Ala-L-Pro-NH₂ 
• 175853-36-8 (5S,8aS)-5-Methyl-hexahydro-3a,6,7-triaza-azulene-4,8-dione 
• 22209-85-4 (2S,2'R)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 792149-87-2 (2R)-alanyl (2S)-prolinamide 
• 27446-57-7 benzyl N-(1S)-2-[(2S)-2-(aminocarbonyl)tetrahydro-1H-pyrrol-1-yl]-1-methyl-2-oxoethylcarbamate 
• 22610-33-9 (2S,2'S)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 81377-00-6 1-Ξ-alanyl-L-proline methyl ester 
• 90107-57-6 C₉H₁₆N₂O₃ 
• 176018-79-4 (5R,8aS)-5-Methyl-hexahydro-3a,6,7-triaza-azulene-4,8-dione 
• 175853-34-6 (2S,2'S)-N-(2'-Bromopropionyl)proline methyl ester 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 

Downstream Products

• 1072102-45-4 C₈H₁₆N₂ 
• 128425-02-5 L-FDAA-L-Pro 

Relevant academic research and scientific papers

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.

Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

Asymmetric synthesis of 3,4,6-trisubstituted 2,5-diketopiperazines by using dynamic kinetic resolution of α-bromo tertiary acetamides

A new and efficient method for the asymmetric synthesis of 3,4,6-trisubstituted 2,5-diketopiperazines has been developed. The dynamic kinetic resolution of L-amino-acid-derived α-bromo tertiary amides in the nucleophilic substitution reaction with p-anisi

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.

Design, synthesis, and structure-activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists

Bicyclic piperazine derivatives were synthesized as conformationally constrained analogs of N-alkyl piperazines and were found to be potent CB1 receptor agonists. The CB1 receptor agonist activity was dependent upon the absolute configuration of the chiral center of the bicyclic ring system. Although the conformational constraint did not protect the compounds from metabolism by N-dealkylation, several bicyclic analogs were found to be more potent than the unconstrained lead compound. Compound 8b demonstrated potent antinociceptive activity in vivo.

Synthesis of fused 1,2,5-triazepine-1,5-diones and some N2- and N3-substituted derivatives: Potential conformational mimetics for cis-peptidyl prolinamides

The synthesis of a new fused 1,2,5-triazepine-1,5-dione heterocycle, which is expected to mimic structural features of cis-peptldyl prolinamides, is described. The required parent heterocycle, corresponding to cis-glycy-(2S)-prolinamide, has been prepared in good yield by the cyclisation of N-(2-bromoacetylprolyl)-hydrazine which is itself generated in situ from the bromoacetyl proline methyl ester. Analogues corresponding to cis-(2R)-alanyl- and cis-(2S)-alanyl-(2S)-prolinamide have been similarly prepared from the appropriate N-(2-bromopropionyl)proline methyl esters and hydrazine hydrate where the cyclisation step, involving the displacement of bromide, has been shown to occur with inversion of configuration at C-2 of the propionyl moiety. Acylation at the N-3 position of the triazepine is equivalent to N-terminal acylation of the residue preceding the proline residue in cis-aminoacyl prolinamides. This has been achieved without incident using standard peptide coupling procedures. Extension at the 'C-terminal' has been achieved by preparing elaborated hydrazine precursors which are reacted with suitably activated esters of N-α-halogenoacylprolines, prior to cyclisation, to give the required fused triazepine dione. Thus it is possible to prepare constrained cis-peptidyl prolyl peptide mimetics of defined stereochemistry based upon this new triazepine dione in which all of the non-proline residues can be varied.

Synthesis and structure of cis-peptidyl prolinamide mimetics based upon 1,2,5-triazepine-3,6-diones

The synthesis of novel constrained cis-peptidyl prolinamide mimetics for the dipeptide amides glycyl (2S)-prolinamide, (2S)-alanyl (2S)-prolinamide and (2R)-alanyl (2S)-prolinamide and some analogues, based upon fused 1,2,5-triazepine-3,6-diones, is described; these are suitable for elaboration into larger peptides at both the carboxy and amino termini, X-ray crystal structures for some of the compounds and intermediates are also presented.

Prevention of Diketopiperazine Formation in Peptide Synthesis by a Simultaneous Deprotection-Coupling Procedure: Entrapment of Reactive Nucleophilic Species by in situ Acylation

Hydrogenolysis of Z-amino acid-D-Pro-OMe dipeptides in the presence of acetic acid results, almost quantitatively, in the formation of diketopiperazines, whereas in the presence of Boc- or 2-(trimethylsilyl)ethoxycarbonyl protected amino acid pentafluorop