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OligoTEA Synthesis, Structure, and Dynamics

Researchers: Emily A. Hoff and Joseph Brown

Sequence-defined Oligomer Synthesis 

In this research thrust, we are interested in efficient assembly schemes for creating sequence-defined polymers. In prior work, we successfully developed a strategy for the assembly of sequence-defined oligothioetheramides (oligoTEAs). In our current and future work, we seek to develop new support-free synthetic approaches to achieve sequence-defined oligomers and macromers.  Support-free, sequence-defined systems are notoriously difficult to obtain, yet we are developing a strategy to eliminate the need to build sequence-defined molecules from a support.  Maintaining sequence specificity without the need for a support will enable the synthesis of precision macromers on a larger scale and address one of the major limitations in the development of sequence-defined polymers. New 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.

OligoTEA Structure and Dynamics

By controlling the relationship between their chemical functionalities and structure, biological macromolecules can be tuned to perform advanced functions. Macromolecular structure is a complex product of intramolecular interactions, entropy, and solvent interactions. Overall, meaningful sequence-structure relationships can help guide the design of functional macromolecules for drug discovery. With sequence-control via oligoTEAs, we are currently working to establish sensitive solution-phase structural characterization to formulate sequence-structure relationships for biological applications. Controlling and characterizing molecular dynamics remains difficult due to the small length- and time-scales, which typically limit experimental structural elucidation techniques. To overcome these difficulties, we currently utilize a combination of variable temperature diffusion spectroscopy (DOSY), electron resonance (ESR) distance measurements, circular dichroism (CD), and small-angle x-ray scattering (SAXS) to examine our oligoTEAs.

Recent Publications

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