- Peptide synthesis in room temperature ionic liquids
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We demonstrate that chemical peptide coupling using modern coupling agents is efficient in rt ionic liquids. This new approach presents some advantages, especially in the case of hindered amino acids, which are not easy to couple under standard conditions
- Vallette, Hélène,Ferron, Laurent,Coquerel, Gérard,Gaumont, Annie-Claude,Plaquevent, Jean-Christophe
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Read Online
- Building Nanowires from Micelles: Hierarchical Self-Assembly of Alternating Amphiphilic Glycopolypeptide Brushes with Pendants of High-Mannose Glycodendron and Oligophenylalanine
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Mimicking the diverse glyco-conjugate structures in nature is always the dream of scientists. Right now, hierarchical self-assembled structures of natural conjugates of peptides and sugars could not easily be achieved via linear glycopolypeptide with mono
- Liu, Yijiang,Zhang, Yufei,Wang, Zheyu,Wang, Jue,Wei, Kongchang,Chen, Guosong,Jiang, Ming
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- Interaction between quaternary ammonium ions and dipeptides: Positive anion allosteric effect
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The binding properties of dipeptides possessing aromatic residues towards quaternary ammonium ions have been investigated by 1H-NMR spectroscopy. The intermolecular hydrogen bonding between exchangeable protons (OH and NH) of aromatic residues
- Ito, Kazuaki,Nagase, Kayo,Morohashi, Naoya,Ohba, Yoshihiro
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- BOMI - A novel peptide coupling reagent
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A novel coupling reagent, benzotriazol-1-yloxy-N,N- dimethylmethaniminium hexachloroantimonate (BOMI), was synthesized and successfully applied to the synthesis of oligopeptides, the racemization and the influence of several reaction parameters such as so
- Li, Peng,Xu, Jie Cheng
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- Expeditious amide-forming reactions using thiol esters
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The reaction of a 2-pyridylthiol ester with a dimethylaluminum amide leads to the rapid formation of the corresponding amide. The tolylthiol esters can be activated with silver trifluoroacetate and coupled even with poorly reactive amino compounds. (C) 20
- Kurosu, Michio
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- Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis
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A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.
- Hollanders, Charlie,Renders, Evelien,Gadais, Charlène,Masullo, Dario,Van Raemdonck, Laurent,Wybon, Clarence C. D.,Martin, Charlotte,Herrebout, Wouter A.,Maes, Bert U. W.,Ballet, Steven
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Read Online
- Tricomponent Supramolecular Multiblock Copolymers with Tunable Composition via Sequential Seeded Growth
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Synthesis of supramolecular block co-polymers (BCP) with small monomers and predictive sequence requires elegant molecular design and synthetic strategies. Herein we report the unparalleled synthesis of tri-component supramolecular BCPs with tunable microstructure by a kinetically controlled sequential seeded supramolecular polymerization of fluorescent π-conjugated monomers. Core-substituted naphthalene diimide (cNDI) derivatives with different core substitutions and appended with β-sheet forming peptide side chains provide perfect monomer design with spectral complementarity, pathway complexity and minimal structural mismatch to synthesize and characterize the multi-component BCPs. The distinct fluorescent nature of various cNDI monomers aids the spectroscopic probing of the seeded growth process and the microscopic visualization of resultant supramolecular BCPs using Structured Illumination Microscopy (SIM). Kinetically controlled sequential seeded supramolecular polymerization presented here is reminiscent of the multi-step synthesis of covalent BCPs via living chain polymerization. These findings provide a promising platform for constructing unique functional organic heterostructures for various optoelectronic and catalytic applications.
- Agasti, Sarit S.,Das, Angshuman,George, Subi J.,Sarkar, Aritra,Sasmal, Ranjan,Venugopal, Akhil
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supporting information
p. 18209 - 18216
(2021/07/10)
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- Crystal structure and supramolecular arrangement of heterochiral tripeptides
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The self-assembly properties of all possible stereoisomers of terminally protected Boc-Val-Phe-Phe-OMe, having sequence homogeneity with Alzheimer's amyloid-beta (Aβ18-20) peptide was investigated. The morphology analysis by field emission scan
- Dolai, Gobinda,Giri, Rajat Subhra,Roy, Sayanta,Mandal, Bhubaneswar
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- Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies
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Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o
- Qin, Minggao,Zhang, Yaqian,Xing, Chao,Yang, Li,Zhao, Changli,Dou, Xiaoqiu,Feng, Chuanliang
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p. 3119 - 3129
(2021/01/20)
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- Transition-metal ion-mediated morphological transformation of pyridine-based peptide nanostructures
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Inspired by natural metallopeptides, we have rationally designed two pyridine-conjugated short peptides. These two peptide conjugates formed a pair of constitutional isomers that helped us describe their structure-function relationship. Both the isomers consisted of an equal number of aromatic amino acid residues, but shuffling was observed in the position of two key amino acids, viz; tyrosine and phenylalanine, which brought a remarkable change in their self-assembling behavior. The presence of specific functional groups and chemical diversity in both conjugates made them very active towards metal coordination. Both the constitutional isomers adopted different pathways of self-assembly, which could be further controlled or transformed by the use of transition metal ions. Interestingly, it was observed that the metal ions could precisely control the morphology of these metallopeptide nanostructures and make them more stable. Therefore, such artificial metallopeptides possess remarkable advantages over the natural counterparts primarily due to their tailor-made chemical structures.
- Singh, Narendra,Singh, Ramesh,Sharma, Swati,Kesharwani, Khushboo,Joshi, Khashti Ballabh,Verma, Sandeep
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supporting information
p. 153 - 161
(2021/01/11)
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- A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides
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Nature provides us a panorama of fibrils with tremendous structural polymorphism from molecular building blocks to hierarchical association behaviors. Despite recent achievements in creating artificial systems with individual building blocks through self-
- Liu, Rongying,Zhang, Ran,Li, Long,Kochovski, Zdravko,Yao, Lintong,Nieh, Mu-Ping,Lu, Yan,Shi, Tongfei,Chen, Guosong
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supporting information
p. 6622 - 6633
(2021/05/29)
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- Controlling Amphiphilic Polymer Folding beyond the Primary Structure with Protein-Mimetic Di(Phenylalanine)
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While methods for polymer synthesis have proliferated, their functionality pales in comparison to natural biopolymers-strategies are limited for building the intricate network of noncovalent interactions necessary to elicit complex, protein-like functions
- Dykeman-Bermingham, Peter A.,Knight, Abigail S.,Warren, Jacqueline L.
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supporting information
p. 13228 - 13234
(2021/09/03)
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- Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers
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The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Al
- Freire, Félix,Qui?oá, Emilio,Riguera, Ricardo,Suárez-Picado, Esteban
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supporting information
p. 4537 - 4543
(2020/02/04)
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- Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis
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Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.
- Morisset, Eléonore,Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 388 - 392
(2020/01/24)
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- Chloride-Assisted Peptide Macrocyclization
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The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtai
- Cindro, Nikola,Horvat, Gordan,Rinkovec, Tamara,Riva, Davide,Speranza, Giovanna,Tomi?i?, Vladislav,Vidovi?, Nikolina
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supporting information
(2020/03/26)
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- Unique crystallographic signatures of Boc-Gly-Phe-Phe-OMe and Boc-Gly-Phg-Phe-OMe and their self-association
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The self-assembly of N- and C-protected tripeptides, Boc-Gly-Phe-Phe-OMe (1) and its analog Boc-Gly-Phg-Phe-OMe (2, Phg = phenylglycine), has been investigated. The presence of just an extra methylene (-CH2-) group in the side chain of one of the amino acids resulted in significant changes in their molecular arrangement and supramolecular structure. The single crystal X-ray diffraction analysis suggested that 1 adopted a type II β-turn-like conformation, known as open turn identified by the absence of any intramolecular hydrogen bond, which further self-assembled to form a herringbone helix-like architecture through non-covalent interactions. To the best of our knowledge, this is the first report on a designed open turn tripeptide without a kink-forming element. However, in spite of the presence of a non-standard amino acid 2 adopted a β-sheet conformation which further self-organized to form a helical architecture through non-covalent interactions in the crystalline form. The conformations of these peptides in solution were also investigated by solvent dependent NMR titration, 2D NOESY, and CD spectroscopic experiments. These peptides exhibited two different flower-like architectures in acetonitrile-water medium under an optical microscope and a field emission scanning electron microscope (FESEM).
- Giri, Rajat Subhra,Mandal, Bhubaneswar
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p. 236 - 243
(2019/01/10)
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- Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct
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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.
- Rajput, Sunnia,McLean, Kirsty J.,Poddar, Harshwardhan,Selvam, Irwin R.,Nagalingam, Gayathri,Triccas, James A.,Levy, Colin W.,Munro, Andrew W.,Hutton, Craig A.
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supporting information
p. 9792 - 9805
(2019/11/13)
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- Pd-Catalyzed Site-Selective C(sp2)-H Olefination and Alkynylation of Phenylalanine Residues in Peptides
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Pd-catalyzed site-selective C(sp2)-H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C-H functionalization. This p
- Zheng, Yong,Song, Weibin
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supporting information
(2019/05/08)
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- MITHRAMYCIN DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
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Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.
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Paragraph 0095; 0122
(2019/04/05)
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- Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides
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The solvatochromic IR responsivity of small side chain –NCS in two unexplored unnatural amino acids, isothiocyanyl alanine (NCSAla = Ita) and lysine (NCSLys = Itl), without perturbing the conformation is demonstrated in two designed
- Bag, Subhendu Sekhar,De, Suranjan
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supporting information
p. 1404 - 1409
(2018/03/23)
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- Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers
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Mithramycin A (1) was identified as the top potential inhibitor of the aberrant ETS transcription factor EWS-FLI1, which causes Ewing sarcoma. Unfortunately, 1 has a narrow therapeutic window, compelling us to seek less toxic and more selective analogues. Here, we used MTMSA (2) to generate analogues via peptide coupling and fragment-based drug development strategies. Cytotoxicity assays in ETS and non-ETS dependent cell lines identified two dipeptide analogues, 60 and 61, with 19.1- and 15.6-fold selectivity, respectively, compared to 1.5-fold for 1. Importantly, the cytotoxicity of 60 and 61 is 100 nM in ETS cells. Molecular assays demonstrated the inhibitory capacity of these analogues against EWS-FLI1 mediated transcription in Ewing sarcoma. Structural analysis shows that positioning the tryptophan residue in a distal position improves selectivity, presumably via interaction with the ETS transcription factor. Thus, these analogues may present new ways to target transcription factors for clinical use.
- Mitra, Prithiba,Eckenrode, Joseph M.,Mandal, Abhisek,Jha, Amit K.,Salem, Shaimaa M.,Leggas, Markos,Rohr, Jürgen
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p. 8001 - 8016
(2018/09/06)
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- A self-assembled tetrapeptide that acts as a “turn-on” fluorescent sensor for Hg2+ ion
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The tetrapeptide (Bz-ΔPhe(p-NPh2)-L-DOPA(protected)-L-Phe-L-Phe-OMe was designed to incorporate seven phenyl rings so that it's conformation, self-assembly and application in Hg2+ ions sensing could be studied. Peptide molecules adopted an overlapping β-turn of type III/III conformation in crystals. The peptide showed a highly selective turn-on response towards mercuric ion over other metal ions with a 10-fold enhancement in fluorescence intensity. This intensity change coupled with the selectivity of the peptide towards mercury allowed us to demonstrate simple colorimetric dip sensing of Hg2+ ions. The technique provides a highly selective and effective way to detect Hg2+ ions. The peptide also self-assembled into nanospheres with diameter ranges from 100 to 500 nm. Mercuric ion coordination enabled these peptide nanospheres to aggregate into well-defined nanoparticles. The enhanced fluorescence upon Hg2+ addition demonstrates that peptide scaffolds can be exploited in the development of different selective sensors.
- Tomar, Kalpana,Kaur, Gagandeep,Verma, Sandeep,Ramanathan, Gurunath
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supporting information
p. 3653 - 3656
(2018/09/11)
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- Pd-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides: Synthesis of indoline-2-carboxylate-containing dipeptides
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A palladium-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino aci
- Zheng, Yong,Song, Weibin,Zhu, Yefu,Wei, Bole,Xuan, Lijiang
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supporting information
p. 2402 - 2405
(2018/04/12)
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- On the Role of Chirality in Guiding the Self-Assembly of Peptides
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Homochirality in peptides is crucial in sustaining “like–like” intermolecular interactions that allow the formation of assemblies and aggregates and is ultimately responsible for the resulting material properties. With the help of a series of stereoisomer
- Basak, Shibaji,Singh, Ishwar,Ferranco, Annaleizle,Syed, Jebreil,Kraatz, Heinz-Bernhard
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supporting information
p. 13288 - 13292
(2017/10/07)
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- Photoinduced electron transfer-promoted debenzylation of phenylalanine and tyrosine derivatives using dicyanoarene
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Photoinduced debenzylations of phenylalanine and tyrosine derivatives with dicyanoarenes afford glycine derivatives by the generation of radical cations. Despite the limited substrate scope, the radical cation of phenylalanine and tyrosine derivatives bearing both a carbamate (without an aromatic group) at the N-terminal and an amide at the C-terminal could promote the breaking C–C bond at the benzylic position by a photoinduced electron transfer. It is important to understand the chemical behavior of the radical cations of phenylalanine and tyrosine in enzymes involving electron transfer.
- Yamawaki, Mugen,Okita, Yoshiki,Yamamoto, Takashi,Morita, Toshio,Yoshimi, Yasuharu
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p. 7239 - 7244
(2017/11/20)
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- Design, synthesis, and characterisation of glyoxylamide-based short peptides as self-assembled gels
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The synthesis and supramolecular properties of novel glyoxylamide-based short peptides formed via the ring-opening reaction of N-acetylisatins in solution phase are described. The short peptides self-assembled into gels, which were examined for their mechanical and morphological characteristics using multiple spectroscopic and microscopy techniques. The critical gel concentration and mechanical strength of the self-assembled gels were influenced by the presence of electronegative substituents (such as fluoro, in 5b) or hydrophobic substituents (such as bromo, 5d) respectively in the short peptides. Moreover, in vitro cytotoxicity assays demonstrated that these compounds were non-toxic to mammalian cells.
- Aldilla, Vina R.,Nizalapur, Shashidhar,Martin, Adam,Marjo, Chris E.,Rich, Anne,Yee, Eugene,Suwannakot, Panthipa,Black, David Stc.,Thordarson, Pall,Kumar, Naresh
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p. 13462 - 13471
(2017/11/27)
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- Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes
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This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes.
- Xin, Bo-Tao,De Bruin, Gerjan,Huber, Eva M.,Besse, Andrej,Florea, Bogdan I.,Filippov, Dmitri V.,Van Der Marel, Gijsbert A.,Kisselev, Alexei F.,Van Der Stelt, Mario,Driessen, Christoph,Groll, Michael,Overkleeft, Herman S.
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supporting information
p. 7177 - 7187
(2016/08/24)
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- NOVEL SHORT-CHAIN PEPTIDES AS KAPPA (κ) OPIOID RECEPTORS (KOR) AGONIST
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The present invention relates to novel short-chain peptides of the general formula (I), which are selective and peripherally acting KOR agonist, their tautomeric forms, their enantiomers, their diastereoisomers, their stereoisomers, their pharmaceutically
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Page/Page column 31; 32
(2016/12/01)
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- Peptide based hydrogels for cancer drug release: Modulation of stiffness, drug release and proteolytic stability of hydrogels by incorporating d-amino acid residue(s)
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Synthetic tripeptide based noncytotoxic hydrogelators have been discovered for releasing an anticancer drug at physiological pH and temparature. Interestingly, gel stiffness, drug release capacity and proteolytic stability of these hydrogels have been suc
- Basu, Kingshuk,Baral, Abhishek,Basak, Shibaji,Dehsorkhi, Ashkan,Nanda, Jayanta,Bhunia, Debmalya,Ghosh, Surajit,Castelletto, Valeria,Hamley, Ian W.,Banerjee, Arindam
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supporting information
p. 5045 - 5048
(2016/04/19)
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- 9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis
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A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy-to-access 9-silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization.
- Aspin, Samuel J.,Taillemaud, Sylvain,Cyr, Patrick,Charette, André B.
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supporting information
p. 13833 - 13837
(2016/10/26)
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- Peptide Mechanosynthesis by Direct Coupling of N-Protected α-Amino Acids with Amino Esters
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In view of developing alternatives to classical peptide synthesis strategies that suffer from low efficacy and negative environmental impact, the reactivity of N-protected α-amino acids, amino esters, and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide was
- Porte, Vincent,Thioloy, Marion,Pigoux, Titouan,Métro, Thomas-Xavier,Martinez, Jean,Lamaty, Frédéric
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supporting information
p. 3505 - 3508
(2016/07/28)
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- Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination
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We describe herein a crystallographic and NMR study of the secondary structural attributes of a β-turn-containing tetra-peptide, Boc-Dmaa-d-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-d-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I′ β-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.
- Metrano,Abascal,Mercado,Paulson,Miller
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supporting information
p. 4816 - 4819
(2016/04/09)
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- 3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester
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A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester.
- Rao, B. Leelamaheswara,Nowshuddin, Shaik,Jha, Anjali,Divi, Murali K.,Rao
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p. 487 - 491
(2016/06/06)
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- Borinic acid catalysed peptide synthesis
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The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.
- El Dine, Tharwat Mohy,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 16084 - 16087
(2015/11/10)
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- An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh3
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A rapid, facile, and efficient mechanochemical synthesis of amides from carboxylic acids has been developed through an in situ acid activation with 2,4,6-trichloro-1,3,5-triazine and a catalytic amount of PPh3. Under room temperature solvent-drop grinding of the reactants in the presence of an inorganic base, a variety of carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids undergo amidation to afford amides in moderate to excellent yields. The method is also compatible with Fmoc, Cbz, and Boc protecting groups which yields protected optically active dipeptides without detectable racemization.
- Duangkamol, Chuthamat,Jaita, Subin,Wangngae, Sirilak,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 52624 - 52628
(2015/06/25)
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- Design, synthesis and preliminary bioactivity studies of imidazolidine-2,4-dione derivatives as Bcl-2 inhibitors
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Anti-apoptotic B-cell lymphoma-2 (Bcl-2) proteins are promising targets for cancer therapy. In the present study, a series of imidazolidine-2,4-dione derivatives were designed and synthesized to test their inhibitory activities against anti-apoptotic Bcl-
- Wang, Gang,Wang, Yutao,Wang, Lei,Han, Leiqiang,Hou, Xuben,Fu, Huansheng,Fang, Hao
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p. 7359 - 7365
(2015/11/27)
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- Self-assembly of a tripeptide into a functional coating that resists fouling
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This communication describes the self-assembly of a tripeptide into a functional coating that resists biofouling. Using this peptide-based coating we were able to prevent protein adsorption and interrupt biofilm formation. This coating can be applied on numerous substrates and therefore can serve in applications related to health care, marine and water treatment.
- Maity, Sibaprasad,Nir, Sivan,Zada, Tal,Reches, Meital
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supporting information
p. 11154 - 11157
(2014/11/08)
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- Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds
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Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.
- Liu, Hui,Yang, Zhimin,Pan, Zhengying
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supporting information
p. 5902 - 5905
(2015/01/08)
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- CHIRAL FLUORINATING REAGENTS
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This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.
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Page/Page column 36
(2014/05/24)
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- Ultrastructure of metallopeptide-based soft spherical morphologies
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Peptides and proteins offer interesting starting points for triggering self-assembly processes owing to the chemical diversity of side-chains, ease of chemical modifications and the possibility of exploiting several non-covalent and metal-assisted interac
- Kaur, Gagandeep,Abramovich, Lihi A.,Gazit, Ehud,Verma, Sandeep
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p. 64457 - 64465
(2015/04/27)
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- Redox-triggered changes in the self-assembly of a ferrocene-peptide conjugate
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Ultrasonication of a ferrocene conjugate of a short amyloid peptide (Aβ18-20) in toluene causes formation of an organogel, which undergoes dramatic structural changes upon oxidation from a nanofibrillar network to spherical micelles. This morphological change is redox-controlled and reversible. the Partner Organisations 2014.
- Adhikari, Bimalendu,Kraatz, Heinz-Bernhard
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supporting information
p. 5551 - 5553
(2014/05/20)
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- A synthetic amino acid residue containing a new oligopeptide-based photosensitive fluorescent organogel
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A synthetic amino acid (with a stilbene residue in the main chain) containing a tripeptide-based organogelator has been discovered. This peptide-based synthetic molecule 1 self-assembles in various organic solvents to form an organogel. The gel has been thoroughly characterized by using various microscopic techniques including field-emission scanning electron microscopy (FESEM), atomic force microscopy (AFM), X-ray diffraction (XRD), UV-visible and fluorescence spectroscopy, and rheology. Morphological investigations using FESEM and AFM show a nanofibrillar network structure. Interestingly, the organogel is photoresponsive and a gel-sol transition occurred by irradiating the gel with UV light of 365 nm for 2 h as shown by the UV and fluorescence study. This photoresponsive fluorescent gel holds promise for new peptide-based soft materials with interesting applications. Copyright
- Maiti, Dibakar Kumar,Banerjee, Arindam
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supporting information
p. 113 - 120
(2013/02/26)
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- Direct amidation of amino acid derivatives catalyzed by arylboronic acids: Applications in dipeptide synthesis
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The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered. Arylboronic acids can be used to catalyze the direct amide formation of protected amino acid derivatives. For less reactive amino acids, cooperative catalysis can be used involving two arylboronic acids, one electron-rich and one electron-deficient, at high catalyst loadings to give good conversions at moderate temperatures. Copyright
- Liu, Shouxin,Yang, Yihua,Liu, Xinwei,Ferdousi, Farhana K.,Batsanov, Andrei S.,Whiting, Andrew
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p. 5692 - 5700
(2013/09/12)
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- Spacer driven morphological twist in Phe-Phe dipeptide conjugates
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Chemists and material scientists are interested in complex biological systems and morphologies for fabrication of new materials. Bioinspired design of short peptide conjugates produces various self-assembled structures, depending on their structural diver
- Ghosh, Surajit,Adler-Abramovich, Lihi,Gazit, Ehud,Verma, Sandeep
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p. 2004 - 2009
(2013/03/13)
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- Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors
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Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50=2.51±0.2 M) showed similar inhibitory effect compared with control compound Bestatin (IC50=6.25±0.4 M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.
- Pan, Huili,Yang, Kanghui,Zhang, Jian,Xu, Yingying,Jiang, Yuqi,Yuan, Yumei,Zhang, Xiaopan,Xu, Wenfang
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p. 717 - 726
(2013/07/26)
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- Hybrid peptides endomophin-2/DAMGO: Design, synthesis and biological evaluation
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Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for μ opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at μ-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro μ affinity (Kiμ = 34 nM), combined with a remarkable in vivo antinociceptive activity.
- Mollica, Adriano,Costante, Roberto,Stefanucci, Azzurra,Pinnen, Francesco,Luisi, Grazia,Pieretti, Stefano,Borsodi, Anna,Bojnik, Engin,Benyhe, Sándor
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p. 167 - 177
(2013/10/01)
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- A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines
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A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.
- Chen, Wenteng,Shao, Jiaan,Hu, Miao,Yu, Wanwan,Giulianotti, Marc A.,Houghten, Richard A.,Yu, Yongping
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p. 970 - 976
(2013/06/05)
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- Environmentally benign peptide synthesis using liquid-assisted ball-milling: Application to the synthesis of Leu-enkephalin
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This paper describes an original methodology for peptide bond synthesis avoiding toxic solvents and reactants. Ball-milling stoichiometric amounts of Boc-protected α-amino acid N-carboxyanhydrides (Boc-AA-NCA) or Boc-protected α-amino acid N-hydroxysuccin
- Bonnamour, Julien,Metro, Thomas-Xavier,Martinez, Jean,Lamaty, Frederic
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supporting information
p. 1116 - 1120
(2013/06/05)
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- Photo-induced charge-transfer complex formation and organogelation by a tripeptide
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A terminally protected tripeptide Boc-Phe-Phe-Tyr-OMe 1 and picric acid form a photo induced charge-transfer complex and organogels. The interactions between stacked aromatic units play a key role in the assembly process. UV light (366 nm) has been used a
- Jana, Poulami,Maity, Sibaprasad,Maity, Suman Kumar,Ghorai, Pradip Kumar,Haldar, Debasish
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experimental part
p. 5621 - 5628
(2012/08/14)
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- An efficient entry to highly substituted chiral 2-oxopiperazines from α-amino acids via iodocyclization
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A short and stereoselective route for the synthesis of 2-oxopiperazines is presented starting from different naturally abundant α-amino acids. The key synthetic steps involved amide coupling, Wittig reaction, HWE olefination, aza-Michael reaction, iodocyc
- Jana, Amit Kumar,Das, Sanjit Kumar,Panda, Gautam
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p. 10114 - 10121,8
(2020/09/02)
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- The cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues
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Endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) is an endogenous tetrapeptide that combines potency and efficacy with high affinity and selectivity toward the μ opioid receptor, the most responsible for analgesic effects in the central nervous system
- Mollica, Adriano,Pinnen, Francesco,Stefanucci, Azzurra,Feliciani, Federica,Campestre, Cristina,Mannina, Luisa,Sobolev, Anatoly P.,Lucente, Gino,Davis, Peg,Lai, Josephine,Ma, Shou-Wu,Porreca, Frank,Hruby, Victor J.
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scheme or table
p. 3027 - 3035
(2012/06/15)
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- Catalytic asymmetric synthesis of substituted morpholines and piperazines
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Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3-substituted morpholines and the diastereoselective synthesis of 2,5-substituted piperazines. Copyright
- Zhai, Huimin,Borzenko, Andrey,Lau, Ying Yin,Ahn, Shin Hye,Schafer, Laurel L.
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supporting information
p. 12219 - 12223
(2013/02/23)
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- PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects
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The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene
- Ding, Ya,Zhang, Peng,Tang, Xiao-Yan,Zhang, Can,Ding, Song,Ye, Hai,Ding, Qi-Long,Shen, Wen-Bin,Ping, Qi-Neng
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experimental part
p. 1694 - 1702
(2012/08/08)
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- Peptide aldehyde inhibitors challenge the substrate specificity of the SARS-coronavirus main protease
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SARS coronavirus main protease (SARS-CoV Mpro) is essential for the replication of the virus and regarded as a major antiviral drug target. The enzyme is a cysteine protease, with a catalytic dyad (Cys-145/His-41) in the active site. Aldehyde i
- Zhu, Lili,George, Shyla,Schmidt, Marco F.,Al-Gharabli, Samer I.,Rademann, J?rg,Hilgenfeld, Rolf
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scheme or table
p. 204 - 212
(2012/05/20)
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