Luk Reports on New Chemoselective Reactions in Water that are Enabling for Future Biomaterials

“Water-Driven Chemoselective Reaction of Squarate Derivatives with Amino Acids and Peptides,” Preeti Sejwal, Yongbin Han, Akshay Shah and Yan-Yeung Luk*, Org. Lett., 2007, 9, 4897-4900.

This work is original and designs an abiotic structure that can proceed with a specific reaction in aqueous environment and in the presence of a mixture of biomolecules in the complex environment. As such, this class of reaction enables three applications.

First, such reagent is of broad usefulness in labeling biomolecules (oligo nucleic acids, peptides or proteins). Because of the chemoselectivity in aqueous environment, and because this reagent is completely soluble and is not degraded by esterase from a biological system, this class of reagents has the potential for efficient labeling targeted molecules in an in vivo environment.

Second, we are using this reaction to immobilize peptides and proteins on surfaces with controlled density and orientation in a bio-inert micro-environment.

Third, we have also validated in our laboratory that this class of molecules provides a rigid core for designing new integrin antagonists, a class of therapeutic agents for a broad range of disease target including cancer and heart problems. Finally, because of the stability and chemoselectivity in aqueous system, this reagent has the potential to be half of a man-designed “life reaction”, in which entirely abiotic reactant structures proceed with extremely high selectivity in a biological system.

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