22 research outputs found

    Metal-driven folding and assembly of a minimal ÎČ-sheet into a 3D-porous honeycomb framework

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    This research was supported by the DST Inspire Faculty Fellowship (No. DST/INSPIRE/04/2020/002499), and National Institute of Pharmaceutical Education and Research, S. A. S. Nagar. S. B. thanks SERB, Govt. of India for the Ramanujan Fellowship (ref. no. RJF/2022/000042) and Ashoka University.In contrast to short helical peptides, constrained peptides, and foldamers, the design and fabrication of crystalline 3D frameworks from the ÎČ-sheet peptides are rare because of their high self-aggregation propensity to form 1D architectures. Herein, we demonstrate the formation of a 3D porous honeycomb framework through the silver coordination of a minimal ÎČ-sheet forming a peptide having terminal metal coordinated 4- and 3-pyridyl ligands.Peer reviewe

    Peptide hydrogen-bonded organic frameworks

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    This research was supported by the DST Inspire Faculty Fellowship (No. DST/INSPIRE/04/2020/002499) from the Department of Science and Technology, New Delhi. R. M. is also thankful to the National Institute of Pharmaceutical Education and Research, S.A.S. Nagar, for providing the research facilities. T. V. thanks Tel Aviv University for the postdoctoral fellowship. E. G. thanks European Research Council PoC project PepZoPower (101101071). A. I. N. thanks the American Chemical Society Petroleum Research Fund (62285-DNI). S. B. thanks SERB, Govt. of India, for the Ramanujan Fellowship (Ref. no. RJF/2022/000042), and Ashoka University, Sonipat, Haryana, for the infrastructure. S. N. acknowledges Vellore Institute of Technology Chennai for the funding and infrastructure.Hydrogen-bonded porous frameworks (HPFs) are versatile porous crystalline frameworks with diverse applications. However, designing chiral assemblies or biocompatible materials poses significant challenges. Peptide-based hydrogen-bonded porous frameworks (P-HPFs) are an exciting alternative to conventional HPFs due to their intrinsic chirality, tunability, biocompatibility, and structural diversity. Flexible, ultra-short peptide-based P-HPFs (composed of 3 or fewer amino acids) exhibit adaptable porous topologies that can accommodate a variety of guest molecules and capture hazardous greenhouse gases. Longer, folded peptides present challenges and opportunities in designing P-HPFs. This review highlights recent developments in P-HPFs using ultra-short peptides, folded peptides, and foldamers, showcasing their utility for gas storage, chiral recognition, chiral separation, and medical applications. It also addresses design challenges and future directions in the field.Peer reviewe

    Four tandem C–H activations: a sequential C–C and C–O bond making via a Pd-catalyzed Cross Dehydrogenative Coupling (CDC) approach

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    An unprecedented aroylation at the ortho C–H bond with respect to a directing group has been accomplished via a Pd(II)-catalyzed cross dehydrogenative coupling approach using alkylbenzene as the synthetic equivalent of an aroyl moiety. The reaction proceeds through sequential C–C and C–O bond making at the expense of four consecutive C–H bond cleavages (three sp<sup>3</sup> benzylic C–H’s and one sp<sup>2</sup> arene C–H) to selectively install an aroyl functionality at the proximal site of substrates containing various directing groups

    Hypervalent Iodine Mediated Synthesis of <i>C</i>‑2 <i>Deoxy</i> Glycosides and Amino Acid Glycoconjugates

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    A simple, efficient, and practical method for the synthesis of <i>C</i>-2 <i>deoxy</i>-2-iodo glycoconjugates in self-assembled structures was found using PhI­(OCOR)<sub>2</sub>. 2-Iodo glycoserinyl esters were intramolecularly converted into 2-iodo serinyl glycosides which upon dehalogenation gave <i>C</i>-2 <i>deoxy</i> amino acid glycoconjugates

    Desulfurization strategy in the construction of azoles possessing additional nitrogen, oxygen or sulfur using a copper(I) catalyst

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    A tandem and convergent approach to various N‐, O‐ or S‐containing azoles has been developed by exploiting the thiophilic property of copper(I) iodide used in a catalytic quantity. The present protocol gives access to amino‐substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter‐ or intramolecular attack of suitable nucleophiles. For aminotetrazoles and triazoles an excellent regioselectivity has been achieved through proper tuning of the pK<sub>a</sub> values of the parent amines attached to unsymmetrical thioureas. The method represents an autocatalytic process in which copper(I) iodide gets converted to copper(II) sulfide which in turn transforms to active copper(II) oxide that effectively carries forward the catalytic cycle. The fate of the copper catalyst has also been studied using Scanning Electron Microscopic (SEM) and Energy‐dispersive X‐ray Spectroscopic (EDS) analyses which give an insight into the mechanism for this catalytic process
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