Sequence-defined Polymers

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Researchers: Pavan Bangalore, Kenton Weigel, Adithya Rangamani, and Meghna Bajaj

Sequence-defined Oligothioetheramide (OligoTEA)

Sequence-structure relationships can help guide the design of functional macromolecules for drug discovery. In this research thrust, we are interested in efficient assembly schemes for creating sequence-defined polymers. We've successfully developed a strategy for the assembly of sequence-defined oligothioetheramides (oligoTEAs). We are currently working to formulate sequence-structure-function relationships and molecular design rules for their use in biological applications. By understanding and controlling the relationship between their chemical functionalities, structure, and interaction with the biological mileu, these novel synthetic constructs can be tuned to perform advanced functions such as transversing the cell membrane barrier, serving as linkers for drug conjugates, and selective disruption of bacterial membranes.

Sequence-defined Oligocarbamate (SeDOC)

Precise sequence and structural control is critical to the development of new functional, responsive and programmable polymeric materials. However, attempts to synthesize unimolecular polymers and precise networks with well-defined sequences are hampered by scale-up limitations. These limitations in scale-up have left research into the impact of sequence on materials largely underexplored. Motivated by these opportunities and the need for sequence-control and structural diversity in polymeric materials research, we have developed a versatile strategy for the assembly of sustainable cross-linkable sequence-defined macromolecules. This new synthetic functional oligocarbamate platform overcomes the scalability issue that plagues the iterative assembly of sequence-defined macromolecules and enables the assembly of oligocarbamate macromers at the gram-scale. Work in this area is done as part of the Center for Sustainable Polymers (CSP) at the University of Minnesota. Please click here for more details on this joint effort.

Recent Publications

Adithya Rangamani and Christopher A. Alabi*. Effect of backbone and end-group regioisomerism on thermomechanical properties of vanillin-based polyurethane networks. Polym. Chem., 2021, DOI: 10.1039/D0PY01578D

Emily A. Hoff, Guilhem X. De Hoe, Christopher M. Mulvaney, Marc A. Hillmyer and Christopher A. Alabi*. Thiol-Ene Networks from Sequence-Defined Polyurethane Macromers. J. Am. Chem. Soc., 2020. DOI: 10.1021/jacs.0c00759

Joseph S. Brown, Andrew W. Ruttinger, Akash J. Vaidya, Christopher A. Alabi and Paulette Clancy. Decomplexation as a rate limitation in the thiol-Michael addition of N-acrylamides. Organic and Biomolecular Chemistry 2020. DOI:10.1039/D0OB00726A

Brown JS, Acevedo YM, He GD, Freed JH, Clancy P, and Alabi CA. Synthesis and Solution Phase Characterization of Sulfonated Oligothioetheramides, Macromolecules 2017. DOI: 10.1021/acs.macromol.7b01915

Porel M, Thornlow DN, Phan NN and Alabi CA. Sequence-defined Bioactive Macrocycles via an Acid-catalysed Cascade Reaction, Nature Chemistry 2016. DOI: 10.1038/nchem.2508

Porel M and Alabi CA. Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks, J. Am. Chem. Soc. 2014, 136 (38), 13162-13165. DOI: 10.1021/ja507262t