2862-51-3Relevant 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
De Zorzi, Rita,Deganutti, Caterina,Garcia, Ana M.,Kralj, Slavko,Kurbasic, Marina,Marchesan, Silvia,Parisi, Evelina,Semeraro, Sabrina
, p. 2839 - 2844 (2019)
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
(2S,5S)-2,5-DIBENZYL-1,4-DIMETHYLPIPERAZINE, A NOVEL ALKALOID FROM ZANTHOXYLUM ARBORESCENCS
Grina, Jonas A.,Stermitz, Frank R.
, p. 5257 - 5258 (1981)
The isolation and structure determination of (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine (1), a new alkaloid biogenetically related to L-phenylalanine diketopiperazine, is described.
Simultaneous synthesis and self-assembly of cyclic diphenylalanine at hydrothermal condition
Togashi, Takanari,Umetsu, Mitsuo,Tsuchizaki, Hiroyuki,Ohara, Satoshi,Naka, Takashi,Adschiri, Tadafumi
, p. 636 - 637 (2006)
Hydrophobic aniino acid, L-phenylalanine, formed insoluble aggregates with unique morphologies at hydrothermal condition. The analyses by infrared spectrum and gel permeation chromatography indicate the highly efficient synthesis of cyclic diphenylalanine
Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group forN-Methylated Cyclic Peptide Production
Cary, Douglas R.,Handa, Michiharu,Kobayashi, Yutaka,Kurasaki, Haruaki,Masuya, Keiichi,Matsuda, Ayumu,Mimori, Yuji,Murase, Shota,Nagaya, Akihiro,Nishizawa, Naoki,Wakui, Kazuya,Yoshino, Madoka
supporting information, p. 2029 - 2038 (2021/09/09)
Herein, we present a new and efficient convergent solution-phase synthetic strategy for producing peptides containingN-methyl amino acids. Specifically, we have synthesized a model cyclic octapeptide with twoN-methyl amino acids, utilizing an isostearyl-m
Solid-state synthesis of cyclo LD-diphenylalanine: A chiral phase built from achiral subunits
Pérez-Mellor, Ariel,Le Barbu-Debus, Katia,Zehnacker, Anne
, p. 693 - 703 (2020/03/10)
The solid-state structure of LL/DD or LD/DL diphenylalanine diluted in KBr pellets is studied by infrared (IR) absorption and vibrational circular dichroism (VCD) spectroscopy. The structure depends on the absolute configuration of the residues. The natural LL diphenylalanine exists as a mixture of neutral and zwitterionic structures, depending on the humidity of the sample, while mostly the zwitterion is observed for LD diphenylalanine whatever the experimental conditions. The system undergoes spontaneous cyclization upon heating at 125°C, resulting to the formation of a diketopiperazine (DKP) dipeptide as the only product. The reaction is faster for LD than for LL diphenylalanine. As expected, LL and DD diphenylalanine react to form the LL and DD enantiomers of cyclo diphenylalanine. Interestingly, the DKP dipeptides formed from the LD or DL diphenylalanine show unexpected optical activity, with opposite VCD spectra for the products formed from the LD and DL reagents. This is explained in terms of chirality synchronization between the monomers within the crystal, which retain the symmetry of the reagent, resulting to the formation of a new chiral phase made from transiently chiral molecules.
Preventing Candida albicans biofilm formation using aromatic-rich piperazines
Simon, Ga?lle,Bérubé, Christopher,Paquet-C?té, Pierre-Alexandre,Grenier, Daniel,Voyer, Normand
, (2020/10/23)
The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm forma
Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct
Rajput, Sunnia,McLean, Kirsty J.,Poddar, Harshwardhan,Selvam, Irwin R.,Nagalingam, Gayathri,Triccas, James A.,Levy, Colin W.,Munro, Andrew W.,Hutton, Craig A.
, p. 9792 - 9805 (2019/11/13)
A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(l-tyrosyl-l-tyrosine) results in sub-μM binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme FeIII. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.
Water-Tolerant and Atom Economical Amide Bond Formation by Metal-Substituted Polyoxometalate Catalysts
De Azambuja, Francisco,Parac-Vogt, Tatjana N.
, p. 10245 - 10252 (2019/11/03)
A simple, safe, and inexpensive amide bond formation directly from nonactivated carboxylic acids and free amines is presented in this work. Readily available Zr(IV)- and Hf(IV)-substituted polyoxometalates (POM) are shown to be catalysts for the amide bond formation reaction under mild conditions, low catalyst loading, and without the use of water scavengers, dry solvents, additives for facilitating the amine attack, or specialized experimental setups commonly employed to remove water. Detailed mechanistic investigations revealed the key role of POM scaffolds which act as inorganic ligands to protect Zr(IV) and Hf(IV) Lewis acidic metals against hydrolysis and preserve their catalytic activity in amide bond formation reactions. The catalysts are compatible with a range of functional groups and heterocycles useful for medicinal, agrochemical, and material chemists. The robustness of the Lewis acid-POM complexes is further supported by the catalyst reuse without loss of activity. This prolific combination of Zr(IV)/Hf(IV) and POMs inaugurates a powerful class of catalysts for the amide bond formation, which overcomes key limitations of previously established Zr(IV)/Hf(IV) salts and boron-based catalysts.
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
Simon, Ga?lle,Bérubé, Christopher,Voyer, Normand,Grenier, Daniel
, p. 2323 - 2331 (2018/12/11)
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.
Radical-Scavenging Antioxidant Cyclic Dipeptides and Silk Fibroin Biomaterials
Manchineella, Shivaprasad,Voshavar, Chandrashekhar,Govindaraju, Thimmaiah
, p. 4363 - 4369 (2017/08/23)
Cyclic dipeptide (CDP) based radical-scavenging antioxidant molecules have been developed through structure–activity screening of rationally designed symmetric and asymmetric aromatic molecules. The antioxidant efficiencies of the designed CDPs were evalu
