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Hydrolysis-resistant proteins with Pictet-Spengler ligations

Pictet-Spengler ligations could be useful for creating hydrolysis-resistant biologics. The Pictet-Spengler ligation forms a hydrolysis-resistant carbon-carbon bond between tryptamine and an aldehyde or ketone. In a protein hydrolysis assay, more than 90% of a stabilized fluorescent protein produced by the Pictet-Spengler ligation remained intact after two days, whereas less than 50% of a fluorescent protein produced using another chemical method remained intact. The ligation reaction generated a HER2 (EGFR2; ErbB2; neu)-targeted antibody-drug conjugate that maintained its target affinity. Next steps could include using the ligation reaction to create additional hydrolysis-resistant variants of existing biologics.

SciBX 6(2); doi:10.1038/scibx.2013.42
Published online Jan. 17, 2013

Patent pending; licensing details available from the University of California, Berkeley Office of Technology Licensing

Agarwal, P. et al. Proc. Natl. Acad. Sci. USA; published online
Dec. 13, 2012;
Contact: Carolyn R. Bertozzi, University of California,
Berkeley, Calif.