35590-65-9

Basic information

• Product Name: 2,5-Piperazinedione, 3,6-dimethyl-, (3R,6S)-rel-
• CAS NO: 35590-65-9
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.158
• Mol File: 35590-65-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2,5-Piperazinedione, 3,6-dimethyl-, (3R,6S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Piperazinedione, 3,6-dimethyl-, (3R,6S)-rel-(35590-65-9)
• EPA Substance Registry System: 2,5-Piperazinedione, 3,6-dimethyl-, (3R,6S)-rel-(35590-65-9)

Safety Data

• Hazardous Substances Data: 35590-65-9(Hazardous Substances Data)

Upstream product

• 7625-53-8 rac-Ala-OMe 
• 10065-72-2 L-Alanine methyl ester 
• 17344-99-9 AlaOEt 
• 3082-75-5 L-Alanine ethyl ester 
• 39825-33-7 isopropyl ester of alanine 
• 39825-33-7 isopropyl L-alanine 
• 124988-44-9 ethyl (R)-2-azidopropionate 
• 2483-51-4 N-[(benzyloxy)carbonyl]-L-alanyl-L-alanine methyl ester 
• 407-25-0 trifluoroacetic anhydride 
• 122748-83-8 Boc-Ala-Ala-O-pentachlorphenylester 
• 64532-72-5 Z-L-Ala-D-Ala-OEt 
• 5845-61-4 cyclo(L-Ala-L-Ala) 
• 28944-89-0 Z-L-Ala-D-Ala-OMe 
• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 95-89-6 2,5-dimethyl-3-chloropyrazine 
• 27023-19-4 2,5-dichloro-3,6-dimethylpyrazine 

Relevant articles and documents

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.

Epimerization of cyclic alanyl-alanine in basic solutions

Alanine anhydrides (Cyclo-(Ala-Ala)) are the simplest dipeptides that have two chiral centers and three diastereomers: Cyclo-(L-Ala-L-Ala), Cyclo-(D-Ala-D-Ala), and Cyclo-(L-Ala-D-Ala). Analysis of the epimerization of these peptides may throw light on the development of homochirality in proteins. We show that the epimerization rate of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) is higher than that of Cyclo-(L-Ala-D-Ala), while the ring-opening rates of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) arelower than that of Cyclo-(L-Ala-D-Ala) in basic aqueous solutions. The total reaction resulted in the preferred stability of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) to Cyclo-(D-Ala-L-Ala).

Stereochemistry of Piperazine-2,5-dione Formation by Self-condensation of DL-Amino Acid Esters

'Racemic' piperazine-2,5-diones (diketopiperazines, dkps) have been synthesized by the self-condensation of DL-amino acid esters without solvent.It was found that 'racemic' dkps consisted of cis- and trans-isomers, and that cis-dkp was preferentially formed in the early stage of the self-condensation, the cis:trans ratios gradually decreasing with increasing reaction time.These results may be attributed to the difference in the rates of cyclization of two kinds of diastereoisomeric dipeptide esters, intermediates in the formation of dkps from DL-amino acid esters.It was further confirmed that the pre-cis-dipeptide ester, which formed cis-dkp, cyclized faster than the pre-trans-dipeptide ester in methanol.Differences in steric hindrance in the cyclization reaction of pre-cis- and pre-trans-isomers may be an important factor in the stereochemistry of self-condensation.