40298-89-3Relevant academic research and scientific papers
Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
supporting information, (2022/01/06)
Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies
Qin, Minggao,Zhang, Yaqian,Xing, Chao,Yang, Li,Zhao, Changli,Dou, Xiaoqiu,Feng, Chuanliang
, p. 3119 - 3129 (2021/01/20)
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
Liquid Phase Peptide Synthesis via One-Pot Nanostar Sieving (PEPSTAR)
Yeo, Jet,Peeva, Ludmila,Chung, Seoyeon,Gaffney, Piers,Kim, Daeok,Luciani, Carla,Tsukanov, Sergey,Seibert, Kevin,Kopach, Michael,Albericio, Fernando,Livingston, Andrew
supporting information, p. 7786 - 7795 (2021/03/01)
Herein, a one-pot liquid phase peptide synthesis featuring iterative addition of amino acids to a “nanostar” support, with organic solvent nanofiltration (OSN) for isolation of the growing peptide after each synthesis cycle is reported. A cycle consists of coupling, Fmoc removal, then sieving out of the reaction by-products via nanofiltration in a reactor-separator, or synthesizer apparatus where no phase or material transfers are required between cycles. The three-armed and monodisperse nanostar facilitates both efficient nanofiltration and real-time reaction monitoring of each process cycle. This enabled the synthesis of peptides more efficiently while retaining the full benefits of liquid phase synthesis. PEPSTAR was validated initially with the synthesis of enkephalin-like model penta- and decapeptides, then octreotate amide and finally octreotate. The crude purities compared favorably to vendor produced samples from solid phase synthesis.
Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers
Freire, Félix,Qui?oá, Emilio,Riguera, Ricardo,Suárez-Picado, Esteban
supporting information, p. 4537 - 4543 (2020/02/04)
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
Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation
Griffiths, Rhys C.,Smith, Frances R.,Long, Jed E.,Williams, Huw E. L.,Layfield, Robert,Mitchell, Nicholas J.
supporting information, p. 23659 - 23667 (2020/10/21)
The development of site-selective chemistry targeting the canonical amino acids enables the controlled installation of desired functionalities into native peptides and proteins. Such techniques facilitate the development of polypeptide conjugates to advance therapeutics, diagnostics, and fundamental science. We report a versatile and selective method to functionalize peptides and proteins through free-radical-mediated dechalcogenation. By exploiting phosphine-induced homolysis of the C?Se and C?S bonds of selenocysteine and cysteine, respectively, we demonstrate the site-selective installation of groups appended to a persistent radical trap. The reaction is rapid, operationally simple, and chemoselective. The resulting aminooxy linker is stable under a variety of conditions and selectively cleavable in the presence of a low-oxidation-state transition metal. We have explored the full scope of this reaction using complex peptide systems and a recombinantly expressed protein.
Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds
Liu, Hui,Yang, Zhimin,Pan, Zhengying
, p. 5902 - 5905 (2015/01/08)
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.
Catalytic asymmetric synthesis of substituted morpholines and piperazines
Zhai, Huimin,Borzenko, Andrey,Lau, Ying Yin,Ahn, Shin Hye,Schafer, Laurel L.
supporting information, p. 12219 - 12223 (2013/02/23)
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
Cross-metathesis of C-glycosides and peptides
Bruechner, Peter,Koch, David,Voigtmann, Ulrike,Blechert, Siegfried
, p. 2757 - 2769 (2008/02/12)
Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerizati
Synthesis of a phenylalanine-rich peptide as potential anthelmintic and cytotoxic agent
Dahiya, Rajiv
, p. 509 - 516 (2008/12/22)
A natural cyclic heptapeptide segetalin D [VIII] was synthesized by coupling of tripeptide unit Boc-Pro-Gly-Leu-OMe [V] with tetrapeptide unit Boc-Ser-Phe-Ala-Phe-OMe [VI] after proper deprotection at carboxyl and amino ends followed by cyclization of linear peptide segment. Structure of VIII was confirmed by spectral and elemental analyses. The newly synthesized cyclopeptide was tested for its antibacterial, antifungal, anthelmintic and cytotoxic activities. Compound VIII showed high cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlichis ascites carcinoma (EAC) cell lines with CTC50 values of 7.54 and 13.56 μM. Moreover, VIII exhibited potent anthelmintic activity against earthworms Eudrilus species, Megascoplex konkanensis and Pontoscotex corethruses at a dose of 2 mg/mL.
Synthesis of Sansalvamide A derivatives and their cytotoxicity in the MSS colon cancer cell line HT-29
Styers, Thomas J.,Kekec, Ahmet,Rodriguez, Rodrigo,Brown, Joseph D.,Cajica, Julia,Pan, Po-Shen,Parry, Emily,Carroll, Chris L.,Medina, Irene,Corral, Ricardo,Lapera, Stephanie,Otrubova, Katerina,Pan, Chung-Mao,McGuire, Kathleen L.,McAlpine, Shelli R.
, p. 5625 - 5631 (2007/10/03)
We report the synthesis of thirty-six Sansalvamide A derivatives, and their biological activity against colon cancer HT-29 cell line, a microsatellite stable (MSS) colon cancer cell-line. The thirty-six compounds can be divided into three subsets, where t
