- Copper(ii) mediated facile and ultra fast peptide synthesis in methanol
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A novel, ultrafast, mild and scalable amide bond formation strategy in methanol using simple thioacids and amines is described. The mechanism suggests that the coupling reactions are initially mediated by CuSO4· 5H2O and subsequently catalyzed by in situ generated copper sulfide. The pure peptides were isolated in satisfactory yields in less than 5 minutes. The Royal Society of Chemistry 2012.
- Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
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- Synthetic minimalistic tryptophan zippers as a chiroptical switch
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In this paper, we presented a new design strategy for a peptide-based chiral supramolecular assembly. A series of aryl linked peptides 1a-1f were designed and synthesized. The bis-urea peptides 1a-1c self-assembled into a helical supramolecular arrangement resembling Trp zipper (Trpzip) structures present in proteins. Interestingly, a dihydrogenphosphate anion, upon binding to the assembly, could invert the chirality of the supramolecular assembly which could be reverted to the original by the addition of water. This chiroptical behavior can be repeated several times. Microscopy analysis showed that the supramolecular helices were assembled to form spheres. In addition to that, we also found that the handedness of supramolecular chirality is dependent on the position of Trp residues on the aromatic scaffold. Both left and right handed helical supramolecular arrangements were obtained by placing l-Trp residues at different positions on the aromatic core. The unprecedented Trpzip in these designed small peptidomimetics will stimulate more work in the area of peptide-based assemblies.
- Haridas,Sadanandan, Sandhya,Dhawan, Sameer,Mishra, Rituraj,Jain, Ishani,Goel, Gaurav,Hu, Yuan,Patel, Sandeep
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- Urea-cored peptides for anion binding and vesicle formation
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Urea and urea-triazole cored peptides were synthesized and characterized. These compounds were analyzed for their potency to sense anions such as F-, Cl-, Br-, I-, H2PO4 - and HSO4 - by UV-
- Bhardwaj, Ishanki,Sapra, Rachit,Haridas
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- A new class of α-ketoamide derivatives with potent anticancer and anti-SARS-CoV-2 activities
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Inhibitors of the proteasome have been extensively studied for their applications in the treatment of human diseases such as hematologic malignancies, autoimmune disorders, and viral infections. Many of the proteasome inhibitors reported in the literature target the non-primed site of proteasome's substrate binding pocket. In this study, we designed, synthesized and characterized a series of novel α-keto phenylamide derivatives aimed at both the primed and non-primed sites of the proteasome. In these derivatives, different substituted phenyl groups at the head group targeting the primed site were incorporated in order to investigate their structure-activity relationship and optimize the potency of α-keto phenylamides. In addition, the biological effects of modifications at the cap moiety, P1, P2 and P3 side chain positions were explored. Many derivatives displayed highly potent biological activities in proteasome inhibition and anticancer activity against a panel of six cancer cell lines, which were further rationalized by molecular modeling analyses. Furthermore, a representative α-ketoamide derivative was tested and found to be active in inhibiting the cellular infection of SARS-CoV-2 which causes the COVID-19 pandemic. These results demonstrate that this new class of α-ketoamide derivatives are potent anticancer agents and provide experimental evidence of the anti-SARS-CoV-2 effect by one of them, thus suggesting a possible new lead to develop antiviral therapeutics for COVID-19.
- An, Jing,Chen, Yiling,Ciechanover, Aaron,Fuk-Woo Chan, Jasper,Huang, Lina S.,Huang, Ziwei,Liang, Boqiang,Nie, Linlin,Wang, Juan,Warshel, Arieh,Wu, Meixian,Wu, Yi,Xu, Yan,Ye, Hui,Yuan, Shuofeng,Yuen, Kwok-Yung,Zhou, Jiao
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- PREPARATION OF 2,4-BIS(METHYLSULFONYL)-1-NAPHTHYL ("BMSN") ACTIVE ESTERS AND THEIR POTENTIAL UTILITY IN PEPTIDE BOND FORMATION
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A convenient synthesis of 2,4-bis(methylthio)-1-naphthol and 2,4-bis(methylsulfonyl)-1-naphthol is reported.The utility of the latter as a carboxyl-activating component in the formation of peptide bonds is also presented.
- Bereznak, James F.,Joullie, Madeleine M.
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p. 3573 - 3578
(2007/10/02)
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