Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins

2009/01/30 by Karina L. Heredia, Gregory N. Grover, Lei Tao +1 · 20 citations
Chemical Engineering · Chemistry · Materials Science · #Advanced Polymer Synthesis and Characterization #Analytical Chemistry and Sensors #Biochemistry #Bioconjugation #Biotin #Biotinylation #Bovine serum albumin #Chain transfer #Chemistry #Chromatography #Combinatorial chemistry #Conjugate #Dispersity #Gel permeation chromatography #Maleimide #Organic chemistry #Polymer #Polymer Surface Interaction Studies #Polymer chemistry #Polymerization #Radical polymerization #Raft #Reversible addition−fragmentation chain-transfer polymerization #Streptavidin

paper · doi:10.1021/ma8022712

openalex publication_date 2009/01/30 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

We describe a straightforward approach to synthesize polymers with end-groups that bind site-specifically to two different proteins. Telechelic biotin−maleimide poly( N -isopropylacrylamide) (pNIPAAm) was synthesized for the formation of streptavidin (SAv)−bovine serum albumin (BSA) polymer conjugates. Reversible addition−fragmentation chain transfer (RAFT) polymerization of NIPAAm was conducted in the presence of biotinylated chain transfer agents (CTAs) with either ester or amide linkages, and the resultant α-biotinylated pNIPAAms were formed with low polydispersity indices (PDI ≤ 1.09). UV−vis analysis of the trithiocarbonate chain-ends indicated 88% or greater retention of the group. A maleimide was introduced to the ω chain-end via a radical cross-coupling reaction with a functionalized azo-initiator. The polymer structures were characterized by 1 H NMR spectroscopy and gel permeation chromatography (GPC). The resultant biotin−maleimide heterotelechelic polymer was used to form a SAv−BSA heterodimer conjugate. Bioconjugate formation was confirmed by gel electrophoresis.

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