Novel class of sequence-defined polymers and preparation methods thereof

Inactive Publication Date: 2021-07-15
INDIAN INST OF TECH PALAKKAD IIT PALAKKAD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes a new type of polymer that can be made using a specific chemical process. This polymer has a unique structure that makes it different from other polymers. The method of making this polymer is simple and efficient, and can be used to create new polymers with different functional groups. This new polymer could have unique properties that make it useful in a variety of applications.

Problems solved by technology

Synthetic sequence-defined polymers possess a wider scope of unlimited functional groups at the side chain and backbone leading to extensive complexity and variable properties.
However, the kinetics of the solid-supported coupling reaction is limited because of diffusion into solid support.
However, it is challenging to have a precise control over the monomer sequence on a synthetic polymer backbone.
Hence, limited number of support-free iterative strategies have been developed so far for SDP synthesis.

Method used

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  • Novel class of sequence-defined polymers and preparation methods thereof
  • Novel class of sequence-defined polymers and preparation methods thereof
  • Novel class of sequence-defined polymers and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

of a 9-Mer (V) of Sequence-Defined Polymer where, R1 is Phenyl Group, R2 is Cyclohexyl Group, R3 is Butyl Group, R4 is Benzyl Group, and R5 is Diethyl Amine Group

[0052]

[0053]Step (a): Synthesis of N, N-diphenyl chloroacetyl amide (2-mer): N, N-Diphenyl amine (1 mmol) was reacted with chloroacetyl chloride (1.5 mmol) in 5 ml of dichloromethane (DCM) and triethylamine. The reaction was carried out at 0° C. for initial 10 min, then the reaction mixture was brought to room temperature and continued for 1 hour at room temperature. After completion of the reaction (monitored by TLC), the excess chloroacetyl chloride was quenched by the addition of sodium bicarbonate (NaHCO3). The reaction mixture was extracted in 1:1 ethyl acetate / water, ethyl acetate layer was dried in anhydrous Na2SO4 and the product was isolated from ethyl acetate layer. The solvent was removed under reduced pressure and the product was used for the next step reaction without further purification.

[0054]Step (b): Synthe...

example 2

of 9-Mer (Va) with R1=Diethyl Amine, R2=Butyl, R3=Cyclohexyl, R4=Benzyl, R5=Pyridine

[0062]

[0063](a) Synthesis of N,N-Diethyl Chloroacetyl Amide (2-Mer):

[0064]N,N-Diethyl amine (1 mmol) was reacted with chloroacetyl chloride (1.5 mmol) in 5 ml of dichloromethane (DCM) and triethylamine. The reaction was carried out at 0° C. for initial 10 min, then the reaction mixture was brought to room temperature and continued for 1 hour at room temperature. After completion of the reaction (monitored by TLC), the excess chloroacetyl chloride was quenched by the addition of sodium bicarbonate (NaHCO3). The reaction mixture was extracted in 1:1 ethyl acetate / water, ethyl acetate layer was dried in anhydrous Na2SO4 and the product was isolated from ethyl acetate layer.

[0065](b) Synthesis of 3-Mer:

[0066]2-mer (1 mmol), the butyl amine-hydroxyl monomer (2 mmol) and CS2 (4 mmol) were mixed in PEG-200 (1 mL). The reaction mixture was stirred at room temperature for 1 h. After completion of the reaction...

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Abstract

The invention provides a new class of synthetic sequence-defined polymer (SDP) and a method of synthesizing the same. The synthetic sequence-defined polymers have dithiocarbamate incorporated to the backbone. The method introduces a functional group dithiocarbamate in the backbone by using a new support-free, protection-deprotection free three-component reaction strategy. Dithiocarbamate-SDP is prepared from a unique bifunctional monomer, CS2 and chloroacetyl chloride. Chloracetyl chloride is used as a co-monomer. Different functional groups may be introduced in the dithiocarbamate-SDP via custom synthesis of monomers with the desired functional group, using the method disclosed. The SDPs may undergo modular post-synthetic modification through multiple paths. SDP is produced in multi-gram scale at low cost and in an eco-friendly manner through the method. No hazardous waste is produced in the process as HCl gas released from the reaction may be neutralized by bicarbonate in the medium.

Description

CROSS-REFERENCES TO RELATED APPLICATIONS[0001]This application claims priority to Indian Patent Application No. 202041001701 filed on Jan. 14, 2020, the full disclosure of which is incorporated herein by reference.FIELD OF THE INVENTION[0002]The present invention relates to sequence-defined polymers, and a method of synthesizing a new class of synthetic sequence-defined polymers thereof.DESCRIPTION OF RELATED ART[0003]Sequence-defined polymer (SDP) is uniform chain of monomers where each monomer unit is at a defined position. Natural sequence-defined polymers are present in a living system as nucleic acids, and proteins with structural and functional complexity. Synthetic sequence-defined polymers possess a wider scope of unlimited functional groups at the side chain and backbone leading to extensive complexity and variable properties. Iterative synthesis is an efficient strategy to precisely control the monomer sequence of sequence-defined polymers in which the growing polymer chai...

Claims

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Application Information

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IPC IPC(8): C08G73/02
CPCC08G73/0253C08G75/28C08G75/00
InventorPOREL, MINTUNANJAN, PANDURANGAN
OwnerINDIAN INST OF TECH PALAKKAD IIT PALAKKAD