Boronic acid functionalized peptidyl synthetic lectins: combinatorial library design, peptide sequencing, and selective glycoprotein recognition
Department of Biochemistry and Molecular Pharmacology
Boronic Acids; *Combinatorial Chemistry Techniques; Glycoproteins; Lectins; Mass Spectrometry; Peptides
Biochemistry | Enzymes and Coenzymes | Medicinal-Pharmaceutical Chemistry | Therapeutics
Aberrant glycosylation of cell membrane and secreted glycoproteins is a hallmark of various disease states, including cancer. The natural lectins currently used in the recognition of these glycoproteins are costly, difficult to produce, and unstable toward rigorous use. Herein we describe the design and synthesis of several boronic acid functionalized peptide-based synthetic lectin (SL) libraries, as well as the optimized methodology for obtaining peptide sequences of these SLs. SL libraries were subsequently used to identify SLs with as high as 5-fold selectivity for various glycoproteins. SLs will inevitably find a role in cancer diagnostics, given that they do not suffer from the drawbacks of natural lectins and that the combinatorial nature of these libraries allows for the identification of an SL for nearly any glycosylated biomolecule.
boronic acids, aberrant glycosylation, synthetic lectins, cancer, sensors
DOI of Published Version
ACS Comb Sci. 2011 May 9;13(3):232-43. doi: 10.1021/co100054e. Link to article on publisher's site. Epub 2011 Mar 25.
ACS combinatorial science
Bicker, Kevin L.; Sun, Jing; Lavigne, John J.; and Thompson, Paul R., "Boronic acid functionalized peptidyl synthetic lectins: combinatorial library design, peptide sequencing, and selective glycoprotein recognition" (2011). Thompson Lab Publications. 51.