Backbone and side chain-linker tunability among dithiocarbamate, ester and amide in sequence-defined oligomers: synthesis and structure–property–function relationship

Jose, Anna; Porel, Mintu

doi:10.1039/d1py01586a

Cited by 2 publications

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“…In addition, this starshaped architecture plays a crucial role in imparting a higher structural stability [20], which makes them an ideal candidate for diverse applications in various fields. Moreover, the incorporation of diverse functionalities in the tuneable backbone can also enhance the potential of SSMs for applications in material and bio-medical sciences [21]. As a Organics 2023, 4 220 proof-of-principle, two important functionalities have been chosen for this study, namely dithiocarbamate (DTC) and triazole units.…”

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confidence: 99%

A Novel Class of Functionally Tuneable Star-Shaped Molecules for Interaction with Multiple Proteins

et al. 2023

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Molecules with tuneable properties are well known for their applications in the material and bio-medical fields; nevertheless, the structural and functional tunability makes them more significant in diverse applications. Herein, we designed and synthesized a novel class of star-shaped molecules via incorporating two important functional groups, i.e., triazole and dithiocarbamate (DTC). The rationale behind selecting these two key functional groups is their diverse applications, e.g., DTC having applications for therapeutics, pesticides, and vulcanizing agents, and triazole having applications for anti-cancer, fungicides, anti-microbials, inhibitors, etc. The structure of the molecules was strategically designed in such a way that their overall structures are the same (central tertiary-amine and peripheral hydroxy groups), except the key functional group (DTC and triazole) in the respective molecules was different. Following synthesis and characterization, the influence of DTC and triazole groups on their bioactivity was compared via interacting with the most abundant proteins present in the blood, including serum albumin, trypsin, haemoglobin, and ribonuclease. From both the experimental and molecular docking studies, it was confirmed that the triazole molecule has a higher binding affinity towards these proteins as compared to the DTC molecule. In summary, two star-shaped DTC- and triazole-based molecules were synthesized and their bioactivity was compared via binding with blood plasma proteins.

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Section: Introductionmentioning

confidence: 99%

A Novel Class of Functionally Tuneable Star-Shaped Molecules for Interaction with Multiple Proteins

et al. 2023

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“…However, the precise sequencing of monomers in the support-free system is quite challenging. Most of the reported support-free strategies for SDPs are based on protection and deprotection chemistry. , Moreover, there are a limited number of SDPs reported having both a support-free and a protection–deprotection-free strategy. − Motivated by the pressing need, we report a support-free and protection–deprotection chemistry-free iterative strategy for SDP synthesis.…”

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Sequence-Defined Tertiary Amine-Based Oligomer Employing a Scalable, Support-Free, and Protection/Deprotection-Free Iterative Strategy

Barik,

Porel

2024

ACS Macro Lett.

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Sequence-defined oligomers (SDOs) with their unique monomeric sequence and customizable nature are attracting the attention of researchers globally. The structural and functional diversity attainable in SDOs makes this platform promising, albeit with challenges in the synthesis. Herein, we report the design and synthesis of a novel class of SDO by incorporating tertiary amines into the backbone from commercially available inexpensive materials. Tertiary amines were selected due to their various material and biomedical applications. Even though the synthesis and purification of amine compounds are challenging, their various significant applications, such as pharmaceuticals, catalysts, surfactants, corrosion inhibitors, dye intermediates, polymer additives, rubber accelerators, gas treating agents, agriculture, and analytical chemistry, make them fascinating. The synthetic strategy that is designed here is extremely efficient and economical for the scalable synthesis of the SDO and is support-free, protection−deprotection chemistry-free, and catalyst/template-free. Most importantly, no extra design and synthesis of the monomer is required here. The key reactions employed for the SDO synthesis are (i) transformation of the hydroxy group to a halide and (ii) substitution of the halide by the secondary amine units. Including the purifying processes, the multigram synthesis of 4-mer was completed in 12−14 h. The synthetic strategy was established by synthesizing two different sequences of SDOs. The SDOs are characterized by 1 H NMR and LC-MS. The tandem MS (MS/MS) experiment was conducted in order to validate the sequences over the SDO chain. Furthermore, the SDO platform was advanced in two ways: (i) by increasing the chain length via attaching a linker, which provides a rapid method for increasing the tertiary amine over the SDO chain, and (ii) postsynthetic modification of SDO with other functional groups, including guanidine for biological importance and a well-known fluorophore dansyl group for material significance.

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Backbone and side chain-linker tunability among dithiocarbamate, ester and amide in sequence-defined oligomers: synthesis and structure–property–function relationship

Abstract: Structural diversity and tunable properties achieved by the defined monomeric sequence are the trademarks of a sequence-defined polymer. Herein, we report a modular synthetic platform where, in addition to the...

Cited by 2 publications

References 30 publications

A Novel Class of Functionally Tuneable Star-Shaped Molecules for Interaction with Multiple Proteins

A Novel Class of Functionally Tuneable Star-Shaped Molecules for Interaction with Multiple Proteins

Sequence-Defined Tertiary Amine-Based Oligomer Employing a Scalable, Support-Free, and Protection/Deprotection-Free Iterative Strategy

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