Facile one-pot preparation of phosphonate functional polythiophene based microsphere via Friedel-Crafts reaction for selective enrichment of phosphopeptides from milk

A novel kind of phosphonate functionalized polythiophene microsphere was designed and fabricated via Friedel-Crafts reaction. Diethyl (thiophen-2-ylmethyl) phosphonate (DTYP) and thiophene were copolymerized by Fe (III) catalysis, without any surfactant, stabilizer and initiator. Functional phosphonate group was directly introduced into the microsphere without redundant modification steps. The adsorption amount of the as-synthesized microsphere, Ti-poly(Th-co-DTYP), was as high as 66.7 mg/g, which was higher than that of commercial Ti4+-IMAC microsphere (49.7 mg/g). The microsphere was explored on the specific capture of phosphopeptides from either tryptic digests of milk or HeLa cell protein. As a result, 88 of unique phosphopeptides mapping to 21 phosphoproteins were identified from 150 mu g of milk tryptic digest after enrichment, and a total of 2534 unique phosphopeptides mapping to 1087 phosphoproteins was identified from HeLa cell. It is expected that such a robust and facile approach will be explored in other functional microspheres to be commercialized in the future. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

A novel phosphonate functionalized polythiophene microsphere was designed and fabricated via Friedel-Crafts reaction, with high adsorption capacity. The microsphere was successfully used for specific capture of phosphopeptides, identifying multiple phosphopeptides from phosphoproteins.