Mousumi Samanta

Ben-Gurion University of the Negev

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Subhajit Bandyopadhyay

Indian Institute of Science Education and Research Kolkata

Suman Kalyan Pal

Indian Institute of Technology Mandi

Joydev Hatai

University of Groningen

Anushri Rananaware

RMIT University

Gonen Ashkenasy

Ben-Gurion University of the Negev

Dinghao Wu

Fujian Inspection and Research Institute for Product Quality

Joydeb Das

Indian Association for the Cultivation of Science

Vagolu Siva Krishna

University of Oslo

Aimee L. Boyle

Leiden University

Karina Abramov‐Harpaz

Ben-Gurion University of the Negev

Cooperative Institutions

Indian Institute of Science Education and Research Kolkata

Ben-Gurion University of the Negev

RMIT University

Indian Institute of Chemical Technology

Leiden University

Indian Institute of Science Bangalore

Madan Mohan Malaviya University of Technology

Goa University

Georgia Institute of Technology

Indian Association for the Cultivation of Science

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Light-triggered assembly–disassembly of an ordered donor–acceptor π-stack using a photoresponsive dimethyldihydropyrene π-switch

Organic & Biomolecular Chemistry (2016)

Vagolu Siva Krishna Mousumi Samanta Suman Kalyan Pal N. P. Anurag Subhajit Bandyopadhyay

A dimethyldihydropyrene based photochromic π-switch in its closed state forms donor–acceptor stacks with 1,4,5,8-naphthalenetetracarboxylic dianhydride. The stacks collapse in the photoisomeric open form.

Acceptor

10.1039/c6ob00101g

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Citations (6)

A Photo‐Switchable Peptide Fibril Esterase

Angewandte Chemie (2024)

Mousumi Samanta Noy Saad Dinghao Wu Niek S. A. Crone Karina Abramov‐Harpaz

Abstract Recent attempts to mimic enzyme catalysis using simple, short peptides have been successful in enhancing various reactions, but the on‐demand, temporal or spatial regulation of such processes by external triggers remains a great challenge. Light irradiation is an ideal trigger for regulating molecular functionality, since it can be precisely manipulated in time and space, and because most reaction mediums do not react to light. We herein report the selection of a photo‐switchable amphiphilic peptide catalyst from a small library of isomeric peptides, each containing an azobenzene‐based light responsive group and a catalytic histidine residue. In its native fibrillar form, the selected peptide is efficiently and enantio‐selectively active for ester hydrolysis, but after irradiation by UV light inducing trans ‐to‐ cis azobenzene isomerization, the fibrils disassemble to amorphous aggregates that are much less catalytically active. Significantly, this esterase‐like activity can be manipulated multiple times, as the fibrillar peptide assembly is reversibly reduced and restored upon alternate irradiation by UV and visible light, respectively. We propose that this research may shine light on the origin of complex functions in early chemical evolution. Furthermore, it paves the way to regulate additional functions for peptide nanotechnology, such as replication, charge transfer, and delivery.

Esterase

10.1002/ange.202413810

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Citations (0)

Asymmetric Aldol Reaction of Thiazole‐Carbaldehydes: Regio‐ and Stereoselective Synthesis of Tubuvalin Analogues

Advanced Synthesis & Catalysis (2014)

Sushovan Paladhi Joydeb Das Mousumi Samanta Jyotirmayee Dash

Abstract The first organocatalytic enantioselective approach to precursors of tubuvaline (pre‐Tuv) is presented employing a prolinamide‐catalyzed aldol reaction of easily accessible thiazole‐carbaldehyde with methyl isopropyl ketone “on water” in excellent yield as well as regio‐ and enantioselectivities. The analogues of pre‐Tuv were achieved using an L ‐proline‐catalyzed direct asymmetric aldol reaction of substituted thiazole‐carbaldehydes with acetone. A direct and flexible approach to the tubavaline (Tuv) core of tubusylins has been established employing the reductive amination of the pre‐Tuv species. The key aldol reaction should greatly expand the potential of this strategy to the synthesis of natural product tubulysins and a range of analogues. magnified image

Aldol reaction

Thiazole

Isopropyl

10.1002/adsc.201400640

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Citations (16)

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Chemical Reviews (2020)

Moran Frenkel‐Pinter Mousumi Samanta Gonen Ashkenasy Luke J. Leman

The fundamental roles that peptides and proteins play in today's biology makes it almost indisputable that peptides were key players in the origin of life. Insofar as it is appropriate to extrapolate back from extant biology to the prebiotic world, one must acknowledge the critical importance that interconnected molecular networks, likely with peptides as key components, would have played in life's origin. In this review, we summarize chemical processes involving peptides that could have contributed to early chemical evolution, with an emphasis on molecular interactions between peptides and other classes of organic molecules. We first summarize mechanisms by which amino acids and similar building blocks could have been produced and elaborated into proto-peptides. Next, non-covalent interactions of peptides with other peptides as well as with nucleic acids, lipids, carbohydrates, metal ions, and aromatic molecules are discussed in relation to the possible roles of such interactions in chemical evolution of structure and function. Finally, we describe research involving structural alternatives to peptides and covalent adducts between amino acids/peptides and other classes of molecules. We propose that ample future breakthroughs in origin-of-life chemistry will stem from investigations of interconnected chemical systems in which synergistic interactions between different classes of molecules emerge.

Abiogenesis

Chemical evolution

Chemical Biology

10.1021/acs.chemrev.9b00664

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A Photoresponsive Glycosidase Mimic and Active Site Mimics of other Hydrolytic Enzymes

Mousumi Samanta Supervisor Dr. Subhajit Bandyopadhyay

This thesis deals with synthesis and studies of the activity of some enzyme active site mimics. Chapter 1 deals with the general introduction on this area of research, background and present scenario of the related work based on recent literature. Chapter 2 comprises of the synthesis of azobenzene-3,3‟-dicarboxylic acid and studies of glycosidase activity in its E and Z forms. The two carboxylic acid groups in the E form deprotonate simultaneously but in case of Z form it occurs in a stepwise fashion. The mono anionic form of the Z isomer acts as an efficient glycosidase mimic at pH 5.8. The mechanism of the reaction proceed via a general acidgeneral base catalysed mechanism. This is the first example of photomodulated glycosidase mimic. Chapter 3 deals with studies of glycosidase activity of a histidine based bipodal ligand. The ligand was found to act as an efficient glucosidase mimic, and displayed a bell-shaped pHrate profile via a general acid-base catalysed mechanism. The mechanism of the reaction was also elucidated. In chapter 4, we demonstrate the phophodiester bond cleavage by a histidine based bipodal catalyst. Similar to the one observed with ribonuclease A, the catalyst can hydrolyse the phosphodiester bonds through a general acidgeneral base catalysed mechanism where one of imidazole ring (Im) which is in the deprotonated form acts as a general base and the other protonated imidazole ring (ImH+) acts as a general base. In all these work, supramolecular association of the substrate with the enzyme active site mimics take place. In Chapter 5, a binding site mimic of an organic cation based on the cation-π interaction was explored. The cation studied was a lysinium cation, and the recetor was based on a tryptophan based bipodal receptor molecule. The positively charged lysine exhibit the cation-π interaction through aromatic box formation. The interaction between the tryptophan residue and the cationic side chain of lysine was studied in details by one and two-dimension NMR methods and emission spectra.

Imidazole

Phosphodiester bond

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CCDC 958704: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Suman Kalyan Pal Joydev Hatai Mousumi Samanta Alok Shaurya Subhajit Bandyopadhyay

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc115lyr

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CCDC 1839412: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Mousumi Samanta Anushri Rananaware Dinesh N. Nadimetla Sk. Atiur Rahaman Monochura Saha

10.5517/ccdc.csd.cc1zr1wn

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A Photo‐Switchable Peptide Fibril Esterase

Angewandte Chemie International Edition (2024)

Mousumi Samanta N. Saad Dinghao Wu Niek S. A. Crone Karina Abramov‐Harpaz

Recent attempts to mimic enzyme catalysis using simple, short peptides have been successful in enhancing various reactions, but the on-demand, temporal or spatial regulation of such processes by external triggers remains a great challenge. Light irradiation is an ideal trigger for regulating molecular functionality, since it can be precisely manipulated in time and space, and because most reaction mediums do not react to light. We herein report the selection of a photo-switchable amphiphilic peptide catalyst from a small library of isomeric peptides, each containing an azobenzene-based light responsive group and a catalytic histidine residue. In its native fibrillar form, the selected peptide is efficiently and enantio-selectively active for ester hydrolysis, but after irradiation by UV light inducing trans-to-cis azobenzene isomerization, the fibrils disassemble to amorphous aggregates that are much less catalytically active. Significantly, this esterase-like activity can be manipulated multiple times, as the fibrillar peptide assembly is reversibly reduced and restored upon alternate irradiation by UV and visible light, respectively. We propose that this research may shine light on the origin of complex functions in early chemical evolution. Furthermore, it paves the way to regulate additional functions for peptide nanotechnology, such as replication, charge transfer, and delivery.

Esterase

Collagen fibril

10.1002/anie.202413810

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Citations (1)

Light triggered encapsulation and release of C60 with a photoswitchable TPE-based supramolecular tweezers

Scientific Reports (2019)

Mousumi Samanta Anushri Rananaware Dinesh N. Nadimetla Sk. Atiur Rahaman Monochura Saha

Abstract Stimuli responsive hosts for C 60 can control its binding and release on demand. A photoswitchable TPE based supramolecular host can encapsulate C 60 in the Z -form with a markedly different visual change in the colour. In addition, the Z -1 bound C 60 has been characterized by various spectroscopic methods and mass spectrometry. Upon exposure to visible light (>490 nm), the host switches to the E -form where the structural complementarity with the guest is destroyed as a result of which the C 60 is disassembled from the host. The results described herein reveals an actionable roadmap to pursue further advances in component self-assembly particularly light-induced association and dissociation of a guest molecule.

On demand

Tweezers

Encapsulation

Molecular machine

10.1038/s41598-019-46242-4

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Citations (14)

Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system

Scientific Reports (2016)

Anushri Rananaware Mousumi Samanta Rajesh S. Bhosale Mohammad Al Kobaisi Biswajit Roy

Abstract The discovery of photoswitchable azobenzene-systems that undergo trans- to- cis photoisomerisation was a milestone in supramolecular chemistry. Such photoswitches have possible applications in data storage, stimuli responsive delivery systems and molecular machines due to fast and selective switching. However, the light induced cis isomer of azobenzene is rather unstable and reverts thermally and photochemically to the thermodynamically stable trans configuration. We report, for the first time, controlled photoswitching of an azo-naphthalenediimide (azo-NDI) which can be achieved upon binding of fluoride ions through anion-π interaction. This NDI-F–NDI “sandwich” stabilises the cis configuration through the generation of an NDI •− radical anion and a dianionic, NDI 2− species that becomes unusually stable in the cis form. The sandwiched cis form reverts to the trans form only upon decomplexation of F − . A model pollutant was successfully degraded using the photogenerated NDI-F–NDI sandwich. This opens a wide range of applications in molecular and supramolecular nanotechnology.

Azobenzene

Molecular machine

Cis–trans isomerism

10.1038/srep22928

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Citations (40)