35590-86-4

Usage

Uses

Used in Pharmaceutical Industry:
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure and stereochemistry make it a valuable intermediate in the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione is used as a chiral intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure can provide novel modes of action and selectivity, leading to more effective and environmentally friendly products.
Used in Chiral Catalysts:
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione can be used as a chiral catalyst in asymmetric synthesis, enabling the production of enantiomerically pure compounds. This can be particularly useful in the synthesis of pharmaceuticals, agrochemicals, and other chiral molecules.
Used in Research and Development:
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione is used as a research tool to study the effects of stereochemistry on biological activity and selectivity. It can help researchers understand the underlying mechanisms of action and develop more effective and targeted therapies.
Used in Flavor and Fragrance Industry:
(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione can be used as a chiral compound in the development of novel flavors and fragrances. Its unique structure and properties can contribute to the creation of new and innovative sensory experiences.

Upstream product

• 216319-94-7 (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione 
• 39614-17-0 L-valyl-L-phenylalanine methyl ester 
• 93510-10-2 ethyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-L-valinate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 20902-47-0 N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 3918-90-9 L-phenylalanyl-L-valine 
• 2754-02-1 N-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-L-valine methyl ester 
• 4070-48-8 L-Valine methyl ester 
• 1202014-18-3 Boc-Phe-Val-O^tBu 
• 1202014-16-1 tert-butyl (S)-2-[(S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino]-3-phenylpropionate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 205517-36-8 (3S,6R)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione 
• 100-39-0 benzyl bromide 

Downstream Products

• 1632153-87-7 (2S,5S)-di-tert-butyl 2-benzyl-5-isopropyl-3,6-dioxopiperazine-1,4-dicarboxylate 
• 17585-69-2 L-phenylalanine hydrochloride 
• 4070-48-8 L-Valine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 72-18-4 L-valine 
• 63-91-2 L-phenylalanine 

Relevant academic research and scientific papers

Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products and Reagents

Dipeptides and their cyclized 2,5-piperazinedione (or diketopiperazine, DKP) derivatives are attractive building blocks for supra-molecular hydrogels. The Phe-Phe, (p -nitro)-Phe-Phe, and Phe-Val dipeptides and their corresponding DKPs are studied for sel

Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.

Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties

Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.

Linear and cyclic dipeptides with antimalarial activity

Several natural and synthetic polypeptides possess important antimalarial activity. Shorter peptides with potent antimalarial activity have also been described, among them linear di-, tri-, tetra- and pentapeptides and their cyclic analogs. In an attempt

Efficient microwave assisted syntheses of 2,5-diketopiperazines in aqueous media

Aqueous in situ one-pot N-Boc-deprotection-cyclization of Nα-Boc-dipeptidyltert-butyl and methyl esters under microwave irradiation afforded 2,5-diketopiperazines (DKPs) in excellent yields. This protocol is rapid, safe, environmentally friendly, and high

Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs (Theobroma cacao)

The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and i

Microwave-assisted synthesis of 2,5-piperazinediones under solvent-free conditions

A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters. Georg Thieme Verlag Stuttgart.

Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2, 5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.

Deracemisation of α-amino acids - (R)- and (S)-phenylalanine from the same enantiomer of a homochiral auxiliary

Chiral auxiliary (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropylpiperazine- 2,5-dione 1 was employed for the synthesis of both enantiomers of phenylalanine using a regioselective deprotonation/stereoselective reprotonation strategy. Modification of this approach enables the efficient deracemisation of (±)-phenylalanine.